摘要:

THE CONSTITUENTS OF AN ESSENTIAL OIL OF RUE. 1585 CLVIIL-The Coiistituents of un Essential Oil of Rice. By FREDERICK B. POWER and FREDERIC H. LEES. THE incentive to this investigation arose from the requirement of preparing some methyl nonyl ketone, the most convenient source of which is the essential oilof rue. A portion of the oil was therefore obtained from an English firm of distillers, and although there was no reason to doubt its purity, i t v a s found to possess some decidedly abnormal characters. As i t bore the designation 01. Rutae Ang., we inferred that not only had the oil been distilled in Britain, but possibly native-grown herb had been used, inasmuch fts the ordinary commer- cial oil appears to be always distilled from fresh material. This afforded a possible explanation of its deviation from the accepted standards of the ordinary oil, and, under these circumstances, i t seemed to merit a more complete investigation. Soon after beginning the work, we observed a brief preliminary notice by Soden and Henle (Phnrm.Zeit., 1901, 277) of an Algerian oil of rue, which was sub- sequently further examined by them (ibid., 1901, 1026). As the oil supplied t o us, on further examination, was found to resemble, in some of its physical and chemical characters, that described by Soden and Henle, we sought information as t o its origin. It was thus ascertained that it had not been distilled from native-grown herb, and as it appears that the rue has never been cultivated in this country for the purpose of distillation, it is highly probable that thesrticle supplied t o us was an Algerian oil.VOL. LXXXI 5 01586 POWER AND LEES: Thoms (Ber. deut. pharm. Ces., 1901, 10, 3) has shown that, besides the chief constituent and the only one which had hitherto been posi- tively identified, namely, methyl nonyl ketone, ordinary oil of rue contains about 5 per cent. of methyl It-heptyl ketone, together with some free fatty acids and a very small amount of a phenol-like sub- stance, from which crystals separated which melted a t 155--156O, but were not further characterised. Soden and Henle (Zoc. cit), in their investigation of the Algerian oil, found that while, like the ordinary European oil, it contains about 90 per cent. of ketones, there is about twice as much methyl heptyl ketone as methyl nonyl ketone. They have also indicated that, ‘‘besides these ketones, the Algerian oil contains a not inconsiderable amount of esters which boil chiefly at 200-210°, and appear to consist, for the most part, of the acetic esters of the secondary alcohols correspond- ing to the two ketones, or of similar aliphatic alcohols, but that they were not yet able to determine the true nature of these esters on account of insufficient material.” I n view of the fact that our investigation of what was assumed to be an English oil had progressed to a considerable extent before the probability of its Algerian origin became apparent, and that we have not only identified the alcohols but also several minor con- stituents, it seemed desirable that the results of the investigation should be recorded. EXP E RIME NT A L.The oil was light yellow in colour ; it had a density d 15*5O/16*= =0-8405, and a,, -3’48‘ in a 100 mm. tube. It was completely soluble in 2 parts of 70 per cent. alcohol. The total amount of oil employed was 1800 grams. Treatment with 30 per cent. Sulphuric Acid.-As Schimmel & Co. (Semi-annwd Report, Oct., 1901, 46) have obtained from ordinary oil of rue a small quantity of a basic oil, possessing a blue fluorescence, which they regarded as methyl methylanthranilate, it seemed desir- able to ascertain whether our oil contained a similar substance. It was therefore extracted with 20 per cent. sulphuric acid, and this liquid made alkaline with sodium carbonate and shaken out with ether. From the ethereal liquid about 0.5 gram of a light brown syrup was obtained, which had an odour suggestive of quinoline or its homologues; it was alkaline to litmus, and caused white fumes in contact with hydrochloric acid.On standing for some time, a few crystals were formed, but were too small in amount to admit of separ- ation. The substance, when dissolved in hydrochloric acid, gave with auric chloride a brownish precipitate, which almost immediatelyTHE CONSTITUENTS OF AN ESSENTIAL OIL OF RUE. 1587 became resinous. It was evident that the basic substance in this oil was not methyl methylanthranilate. Treatment with Sodium Carbonate.-In order t o separate any un- combined fatty acids, the oil was subsequently extracted with a 5 per cent. solution of sodium carbonate. The alkaline liquid was concentrated? acidified with sulphuric acid, and distilled with steam.The distillate, which contained oily drops, was shaken out with ether, and from the ethereal liquid a small amount of a light brown oil was obtained. This, on distillation, gave two fractions : (I) below 200°, and (2) 220-270O. These were converted into silver salts of which one salt (a) was pre- pared from fraction (I), and two salts ( b ) and (c), from fraction (2). They were respectively well washed, dried, and analysed : (a) 0.0601 gave 0.0262 Ag. Ag = 43.5 per cent. (b) 0.1004 ,, 0.0390 Ag. Ag=38.8 ,, (c) 0 0948 ,, 0.0400 Ag. Ag=42.2 ,, It was evident from these results that the free fatty acids con- tained in the oil consist of a mixture, the constituents of which were too small in amount t o admit of identification. Idemtzycation of Hethyl Salicylute.Treatment with Potassium Hydroxide.-After the treatment with sodium carbonate, the oil was extracted with a 5 per cent. solution of potassium hydroxide. The alkaline liquid was acidified with sulphuric acid and extracted with ether. The ethereal liquid afforded a small amount of a dark brown oil, which had the characteristic odour of methyl salicylate, and on standing a short time formed a crystalline paste. This was spread on a porous tile, when the oily mother liquor was removed and a small quantity of white crystals obtained, which, after recrystallisation from hot water, melted at 155-156', gave a deep violet colour with ferric chloride, and were identified as salicylic acid.* On analysis : 0,1304 gave 0.2899 CO, and 0.0528 H,O.C = 60.6 ; H = 4.5. C,H608 requires C = 60.9 ; H = 4.4 per cent. From the porous tile, by extraction with warm ether, a small amount of an oily liquid was obtained which distilled between 190' and 250' This, on hydrolysis, yielded a further amount of salicylic acid. As the original oil had been previously extracted with sodium car- bonate, the salicylic acid could not have existed in it as such, but must * The substance obtained by Thoms (Zoc. cit.), which melted a t 155-156", wonld also appear to have been salicylic acid. 5 0 2I588 POWER AND LEES: have been present as an ester which had become partially hydrolysed in the process of isolation. It was evident that this ester was methyl salicylate. Ketonic Constituents of the Oil.Treatment with h'odium Bisulphite.-The ;whole of the oil, after the treatment just described, was diluted with ether and then repeatedly shaken with a saturated solution of sodium bisulphite. The crystal- line compound was well washed with ether, drained, and pressed. The combined ethereal filtrate and washings were first shaken wibh a solu- tion of sodium carbonate t o remove sulphurous acid, then with water, finalIy dried with calcium chloride, and the ether removed. The residual oil, thus deprived of the larger portion of its ketonic conetitu- ents, 'was set aside for subsequent examination. The bisulphite compound was suspended in ether and decomposed with a 10 per cent. solution of sodium hydroxide. The ethereal solu- tion was washed with water, dried with calcium chloride, and the ether removed.The residual oil was then fractionally distilled. After pro- longed fractionation, it was resolved chiefly into two large fractions, one distilling at 190-200' and the other at 225-235'. Identification of Methyl n-Heptyl Ketone. Fraction 1 90-200°.-On redistilling this fraction, the greater part boiled a t 194-197'; it was most constant at 1945-195.5' under 763 mm. pressure and this portion had a density d 14°/160==0*8296. On analysis : 0,0934 gave 0:2617 CO, and 0-1080 H,O. The semicarbazone melted at 119--120*. 0.1272 gave 0.2790 CO, and 0.1214 H,O. C = 76.4 ; H= 12.8. C9H,,0 requires C = 76.1 ; H = 12.7 per cent. On analysis : C = 59.8 ; H = 10.6. C,,,H,,ON, requires C = 60.3 ; H = 10.6 per cent. Identification of Methyl n-Nonyl Ketone.Traction 225--235'.-0n redistilling this fraction, i t boiled for the The semicarbazone melted at 122O. 0.1376 gave 0.3195 00, and 0.1358 H,O. C,,H,,ON, requires C = 63.4 ; H = 11.0 per cent. The boiling point of methyl nonyl ketone is generally stated t o be 224' ; Thoms (Zoc. cit.) likewise records it as 223-224' under 774 mm. most part at 229-233' under 759'mm. pressure. On analysis : C = 63.3 ; H = 11.0.THE CONSTITUENTS OF AN ESSENTIAL OIL OF RUE. 1589 pressure, whereas Soden and Henle (Zoc. cit.) have indicated it to be 230-231' under 740 mm. pressure. We have confirmed this observa- tion by regenerating the ketone from the repeatedly crystallised semi- carbazone ; it then distilled completely at 231.5-232*5' under 761 mm.pressure, and had a density d 20-5°/160 = 0.8263. On analysis : 0.0845 gave 0.2398 GO, and 0.0994 H,O. C = 77.4 ; H= 13.1. C,,H,,O requires C = 77.6 ; H = 12.9 per cent. Non-htonic Constituents of the Oil. The portion of the original oil which did not combine with sodium bisulphite was subjected to fractional distillation. Under the ordinary pressure, a portion distilled over below 207' ; this on further distillation afforded the following fractions : 120-145', 145-165', 165-170', 170-180', and 180-185'. The portion distilling above 185' was finally mixed with that which boiled above 207" in the first instance. Tractions 120-145', 145-165', and 165-170°.-These fractions were examined as follows : Rraction 120-145°.-This had a density d 16'/16' = 0.8416 and was optically inactive.On analysis : 0,0932 gave 0.2516 CO, and 0.0987 H20. C= 73.6 ; H = 11.8. Rmction 145-1 65'.-This had a density d 16O/ 16' = 0.852 and On analysis : aD -2'45' in a 25 mm. tube. 0,098 gave 0.282 CO, and 0.106 H,O. C = 78.5 ; H = 12.0. These two fractions had a combined weight of not more than They possessed an odour of terpene and also one recalling 5 grams. that of ethyl valerate. Ident$cation of cb Vderic Estey. The above two fractions were mixed and boiled for some hours with a dilute aqueous solution of potassium hydroxide. There still floated on the surface of the liquid a considerable proportion of the oil, which was taken up with ether and examined in connection with the fraction boiling at 165-170'. The alkaline liquid was acidified, and again extracted with ether, which dissolved a small amount of a fatty acid from which a silver salt was prepared.This by recrystallisation from hot water was separated into three fractions, which were analysed : (1) 0.0638 gave 0.0324 Ag. Ag = 50.8. (2) 0.0558 ,, 0.0287 Ag. Ag=51*4. It was thus evident that the oil contained an exceedingly small C,H:,O,Ag requires Ag = 51.7 per cent. amount of a valeric ester, which was probably ethyl valerate.1590 POWER AND LEES: Iclentijcation of Pinene. The oil separated by the hydrolysis of the two preceding fractions, 120-145' and 145--165O, was mixed with the small fraction 165-1'70O. The total liquid, which amounted to 3 grams, evidently contained a terpene, and from it a small amount of a nitrosochloride was prepared, The latter was converted into the nitrolepiperidide which, after recrystallisation from methyl alcohol, melted at Identijcation of Limonene and Cineol.11 9-1 20'. Practions 170--1 80' and 180--185°.--These two fractions weighed Traction 170-18O0.-This had a density d 15*5'/16O = 0.8606 and (1) 0,1306 gave 0.3987 CO, and 0.1405 H,O. Fraction 180-185°.-This had a density d 15*5O/16'= 0.8588 and uD - 10'30' in a 25 mm. tube. Both these fractions were insoluble in 70 per cent. alcohol, and were otherwise practically identical. Their general characters indi- cated that they contained a considerable proportion of a terpene, but they also had an odour suggesting the presence of cineol. The presence of limonene in the two preceding Fractions was deter- mined by means of the tetrabromide, which melted at 103'; the high laevorotation of the fractions made it evident that it mas I-limonene." The fraction 170-180" was specially tested for phellandrene, but with a negative result.The identification of cineol in these two fractions was effected by means of its compound, C,,H,,O C,I,NH, with t et raiodopyrrole (Hirschsohn, Pharm. Zeit. RUSS., 1893, 32, 49, 67), and also by the additive product with hydrogen bromide. The former melted with decomposition at 114-115', and the latter a t 55-56'. On warming the hydrobromide with dilute alkali, it developed the unmistakable odour of cineol. respectively 11 and 5 grams, and had the following characters : uD -20'16' in a 50 mm. tube. On analysis : C = 83.3 ; H = 12.0. (2) 0,1238 ,, 0.3780 CO, ,, 0.1340 H,O.C=83*3; H=12*0. Portion of Oil boiling above 185O.-This was hydrolysed with alcoholic potassium hydroxide.' The alcohol was then removed, water added, * It is stated in " Die aetherischen Oele," by Gildemeister and Hoffmann, p. 596, that ( ' the terpene found in oil of rue by different investigators is in all cases to be referred to an adulteration with oil of turpentine," and Thorns (Zoc. cit.) also states that it contains no terpene. No constituent of the genuine oil has, however, hitherto been isolated which would account for its optical activity, and the possi- bility of the presence of a small amount of terpene would therefore not seem to be excluded.THE CONSTITUENTS OF AN ESSENTIAL OIL O F RUE. 1591 and the separated oil taken up with ether.The ethereal solution was washed, dried quickly with calcium chloride, and the ether removed. The alkaline liquid was acidified, distilled with steam, and the dis- tillate neutralised with sodium carbonate, concentrated, acidified, and extracted with ether. From the ethereal solution a n appreciable quantity of a light yellow, pungent liquid was obtained. This distilled almost completely below 120°, leaving a very small amount of an acid of higher boiling point in the flask. Ident$cation of Acetic Acid. The portion of acid which distilled below 120' was converted into its barium salt, and from a portion of this a silver salt was prepared. On analysis : 0.2208 gave 0,1426 Ag. Ag= 64.6. C,H,O,Ag requires Ag = 64.7 per cent. The higher boiling portion of volatile acid was dissolved in a little dilute aqueous ammonia, decolorised by animal charcoal, and converted into a silver salt, which was for the most part insoluble in hot water.On analysis : 0.0704 gave 0.0304 Ag. The small amount of this acid did not permit of its identification. Ag= 43.2 per cent. 5% Alcohols. The oil obtained by the above hydrolysis, when tested with semicarb- azide, was found still to contain a considerable amount of ketone, not- withstanding the previous exhaustive treatment with bisulphite. A preliminary distillation showed that the greater part passed over be- tween 190' and 250'; that boiling above 250', which will be subse- quently referred to, possessed a beautiful indigo-blue colour. The oil was therefore fractionally distilled until that passing over below 250' was quite free from any blue colour.I n order to separate from this oil the last portion of ketones, recourse was had to the following method. 20.7 Grams of sodium were dissolved in 250 C.C. of absolute alcohol, and 100 grams of semicarbazide hydrochloride, made into a paste with alcohol, were introduced. An alcoholic solution of semicarbazide was thus obtained, sufficient in amount t o combine with the 128 grams of oil employed, had the latter consisted entirely of methyl heptyl ketone. This mixture was boiled for half an hour, and then, while still hot, filtered from the sodium chloride. On concentrating the filtrate, a considerable amount of the crystalline semicarbazones separated, which1.592 POWER AND LEES: was removed by means of a pump, and washed well with cold alcohol. On the addition of water to the filtrate, there separated the substances which had not combined with the semicarbazide, together with a small amount of the semicarbazones.These were taken up with ether, which was subsequently removed, and the oily residue rapidly dis- tilled in steam, The non-ketonic substances quickly came over, and i t was only after these had distilled that the semicarbazones began slowly to decompose, The oil was extracted with ether, dried with potassium carbonate, and, after the removal of the ether, fractionally distilled. The principal fractions were collected at 1 90-200' and 220-235', and of these the latter was much smaller than the former. Smaller fractions were also collected a t 200-205', 205-210', and 2 10-220'.IdentiJication of Nethyl -n-hept ylcadinol. Fraction 1 90-200°, on redistillation, yielded a fraction boiling con- (1) 0.0931 gave 0.2605 GO, and 0.1 130 H,O. Fvaction 200-205°.--'L'his was also analysed : 0.1007 gave 0.2780 CO, and 0.1258 H,O. As the principal fraction was evidently not quite pure, the separa- tion of any trace of terpene it might still contain was effected by converting the alcohol into its acetic ester. Por this purpose, the two fractions were mixed and boiled with an equal weight of acetic anhydride and a little anhydrous sodium acetate. A product was thus obtained which distilled chiefly at 212-217', and most constantly at 213-215'. This was analysed : stantly at 195-196'. On analysis : C = 76.3 ; H = 13.5.(2) 0.1048 ,, 0.2931 CO, ,, 0.1285 H20. C=76.3; H=13*6. C = 75.3 ; H= 13.9. C,H,,O requires C = 75.0 ; H = 13.9 per cent. 0.1210 gave 0.3174 GO, and 0.1300 .H20. C,,H,,O, requires C = 71*0 ; H = 11.8 per cent. Methyl-n-heptylcarbinyl ucetate, CH,*CH(O*C,H,0)*C7H15, was a colourless oil of pleasant odour, and had a density d 20m5*/16*= 0.8605 and aD - 3'3' in a 50 mm. tube. Hydrolysis afforded methyl-n-heptyl carbinol, which boiled at 198-200' under 765 mm. pressure, and had a density d 19'/16' = 0.8273 and aD - 3'44' in a 50 mm. tube. 0.1223 gave 0.3348 GO, and 0,1529 H,O. On oxidation with chromic acid, this optically active alcohol afforded C=71*5; H=11*9. On analysis : C= 74.7 ; H= 13.9. C,H,,O requires C = 75.0 ; H = 13.9 per cent.THE CONSTITUENTS OF AN ESSENTIAL OIL OF RUE.1593 methyl n-heptgl ketone, which had the characteristic odour, distilled a t 195-199O, and yielded a semicarbazone melting at 118-1 1 9'. The proof was thus afforded that this alcohol is methyl-a-heptylcarbinol. IdentiJccction of Methy I-n-non ylcarbinol. The fraction boiling a t 220-235' was relatively very small in amount. It was acetylated, as in the case of the alcohol of lower boiling point. The product, on fractionation, distilled principally between 240° and 248', and was most constant at 245'. Hydrolysis afforded the alcohol, which boiled a t 230-235', and was most constant at 231-233't; i t had ccD - 1'18' in a 25 mm. tube, This fraction was analysed : 0.0991 gave 0,2793 GO, and 9.1220 H20. This optically acbive alcohol afforded, on oxidation with chromic It was C = 76.9 ; H= 13.7.C,,H,,O requires C = 76.7 ; H = 14.0 per cent. acid, a ketone, which formed an oxime melting a t 46-47'. thus identified as methyl-n-nonylcar binol. A Blue Oil. It has already been noted that from that portion of the oil used for the identification of the alcohols a fraction was separated, boiling above 250C; which possessed a deep blue colour. I t was relatively small in amount, and had a rank, weed-like odour. On redistillation, it passed over between 250' and 320°, but was at no point constant. Theliquid was dichroic, the colour, in r e d ~ t e d ~ l i g h t , being a deep indigo-blue? and in transmitted light, red. It was sparingly soluble in 70 per cent. alcohol. When dissolved in glacial acetic acid, it gave a reddish- brown colour on the addition of a drop of hydrochloric acid.The presence of a blue oil in a n oil of rue has not hitherto been observed. The small amount, and the complex character of this liquid, rendered it impossible t o determine its composition. sumrnury . From the preceding details it will be seen that this essential oil of rue, which mas apparently of Algerian origin, contained the following substances : 1. Methyl-n-hegtylketone. 2. Methyl-n-nonylketone. 3. Methyl-n-heptylcarbinol . 4. Methyl-m-nonylcar binol. 5. A blue oil of high and inconstant boiling point.1594 LEES : METEYL P-METHYLHEXYL KETONE. 6. Acetic acid, in combination with the alcohols. 7. A basic substance, having the odour of quinoline. 8. A mixture of free fatty acids. 9. Methyl salicylate. 10. Ester of valeric acid, apparently ethyl valerate. 11. Pinene. 12. I-Limonene. 13. Cineol. The relative proportion of the above constituents is approximately as follows : The two ketones represented 80 per cent. of the oil, and were present in about equal amounts. The two alcohols represented about 10 per cent., and were present partly in the uncombined state and partly as acetic esters. The methyl-wheptylcarbinol preponderated. The two terpenes, together with cineol, represented about 1 per cent. of the oil. There was very little pinene, and the amounts of limonene and cineol were about equal. The amount of blue oil was about 0.5 per cent., and finally there was separated from the non-ketonic portion of the oil a small amount of undistillable, viscous substance, which was probably a decomposition product. The fact that the substances associated with the ketones and alcohols are present in such small amount, and that the limonene is the more rarely occurring I-form, enables us to conclude that all these substances are natural constituents of the oil. THE WXLLCOME CHEMICAL RESEARCH LABORATORIES.

ISSN:0368-1645    

DOI:10.1039/CT9028101585

出版商:RSC    

年代:1902

数据来源: RSC

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1594 LEES : METEYL P-METHYLHEXYL KETONE. C L I X . --Met J?yl ,&Net JL y I hex y I Ketone. By FREDERIC HERBERT LEES. IN the course of an investigation of the ketones contained in an essential oil of rue (this vol., p. 1585), methyl P-methylhexyl ketone, CH,-CO*CH2*CH(CH3)*[CH2]3*GH3, mas prepared and characterised. It was obtained by the hydrolysis of ethyl see,-hexylacetoacetate, CH,*CO*CH(C,H,,)*CO,Et, which was prepared by the condensa- tion of see.-hexyl iodide (from mannitol) with ethyl acetoacetate. Ethyl sec. -hexyZacetoacetate.-Sodium (5.8 grams) was dissolved in absolute alcohol (60 c.c.), and to the solution mere successively adde'h, ethyl acetoacetate (3'2.5 grams), and sec.-hexyl iodide (53 grams). TheLEES : METHYL P-METHYLHEXYL KETONE. 1595 resulting clear liquid was then heated in a soda-watef bottle at 100' for 14 hours, when the product became neutral.The greater part of the alcohol was removed by distillation, water was then added, and the precipitated oil taken up with ether. The ethereal solution was washed with water, dried with calcium chloride, and the ether removed. The residue was then fractionally distilled under diminished pressure, when a quantity of the pure substance, amounting to 30 per cent. of that theoretically obtainable, distilled as a nearly colourless oil at 130-132' under 17 mm. pressure, Under the ordinary pressure, it boiled a t 243-245O. Its alcoholic solution gave a brown coloration with ferric chloride. On analysis : 0.131 gave 0.3198 CO, and 0.1 185 H,O. C,,H,,O, requires C = 67.3 ; H = 10.3 per cent.Methyl P-Methylhexyl Ketone.-Ethyl sec.-hexylacetoacetate (16 grams) was boiled with a solution of potassium hydroxide (10 grams) in water (20 c.c.) for nine hours. The oil was then dissolved in ether, the ethereal solution washed with water, dried with calcium chloride, and the ether removed, The residual oil was then fraction ated, when the ketone was obtained, to the extent of 80 per cent. of the theoretical, as a colourless, pleasantly odorous liquid, which boiled at 184O under 769 mm. pressure. A density determination gave d 15'/16O -0.8319. On analysis: C = 66.6 ; H = 10.1. 0.127 gave 0.3538 CO, and 0.1447 H,O. The semicarbazone, recrystallised from petroleum, formed rosettes of 0,1804 gave 0.4 CO, and 0.1728 H,O. C = 60.5 ; H= 10.6. The oxime, at the ordinary temperature, is a colourless oil. 0.1482 gave 0.3128 GO, and 0.1606 K,O. C = 68.6 ; H = 12.0. C = 76.0 ; H = 12.7. CgH,,O requires C = 76.1; H = 12.7 per cent. fine needles and melted a t 7 5 O . On analysis : C,,H,,ON, requires C = 60.3 ; H = 10.6 per cent. On analysis : CgH,,ON requires C = 68.8 ; H = 12.1 per cent. THE WELLCOME CHEMICAL RESEARCH LABORATORIES.

ISSN:0368-1645    

DOI:10.1039/CT9028101594

出版商:RSC    

年代:1902

数据来源: RSC

摘要:

1596 WADE : THE CONSTITUTION OF THE METALLIC CYANIDES. cLX.-T%e Constitution of the Metallic Cyanides as Deduced from their Synthetic Interactions : The Con- stitutioii o f Hydrogen Cyanide. By JOHN WADE, D.Sc. THE simplest view of the constitution of the metallic cyanides is that which Frankland and Kolbe established when they proved the identity of the alkyl cyanides with the nitriles of the fatty series (1Nem. Chem. Xoc., 1847, 3, 386). Pelouze had made the first of these compounds from potassium cyanide and barium ethylsulphate (A.lznaZem, 1834, 10, 249), and it followed from Frankland and Kolbe’s work that the nitriles contain the cyano-group, and are akin to the metallic salts. H*CiN + M-CiN -+ R*CiN. The subsequent synthesis of propionitrile from potassium cyanide and ethyl iodide (Buckton and Hofmann, this Journal, 1856, 9, 241) confirmed this conclusion, and it was only when Gautier proved that the silver salt yields an isomeric product (BUZZ.Xoc. Chim., 1865, [ii], 4, 88) that the problem arose which forms the subject of the present paper. The formation of isocyanides (carbylamines) from silver cyanide showed equally clearly, however, that the metallic salts may possess the isocyanic constitution, a possibility also indirectly supported by some ob- servations of Gautier (Compt. rend., lt367, 65,468) and Hofmann (Proc. Roy. Soc,, 1868, 16, 150). These chemists found that the isocyanides may contain small quantities of nitriles, the inference being (compare Schorlemmer’s Chemistry of the Carbon Compounds, 1874, p. 93) t h a t the latter in every case are secondary products, which are formed from the isocyanides by isomeric change (1).Gautier pointed out, however (Ann. Chim. Yhys., 1869, [iv], 1’7, 103), that the chemical behaviour of hydrogen cyanide is that of a nitrile, and concluded that the acid corresponding with the metallic (iso) cyanides is unknown. (1) (H*N:C) ++ M*N:C + R*N:C -+ R*CiN. No further solution appears to have been offered until Laar intro- duced the hypothesis of tautomerism (Ber., 1885, 18, 648). Gautier had proved that hydrogen cyanide is one substance, whether prepared from potassium cyanide or the silver salt (Ann. China. Phys., Zoc. cit.), but Laar pointed out that if its hydrogen atom be supposed to oscillate, the acid may possess either constitution (2j, and thus yield both classes of alkyl cyanides as primary products.H G i N f-, K-CiN -+ R-CiN (’) c€€*N:C f-, Ag-N:C --f R*N:C *WADE: THE CONSTITUTION OF THE METALTJC CYANIDES. 1597 A third solution has been given by Nef (Annulen, 1892, 270, 329), introducing the idea of intermediate additive compounds. Nef xttri- butes the formation of nitriles from the metallic (iso) cyanides to the unsaturated condition of the carbon of the latter (3) ; the isocyanides are alone formed by substitution, and the acid is assumed [Amnalen, 1895, 287, 325) to belong t o the same class. 4+ Ag*N:C -+ R*N:C (3) H*N:C- K*N:C -+ K~N:C<: -+ KI+NX*R There are thus three hypotheses which give an account of the am- biguous behaviour of the metallic cyanides, and the work which is described in this paper was undertaken in order to decide between them.I, 11. Both nitriles and isocyanides are formed from potassium cyanide, but the conditions under which the isocyanides are converted into nitriles show that the hypothesis of isomeric change (1) is inadequate. 111. The contradictory behaviour of silver cyanide with alkyl and acyl compounds is not explained by the tautomerism of hydrogen cyanide (Z), but would necessitate the tautomerism of the salt itself, if direct interchange of radicles be assumed. IV, VI. The general actions of the alkali cyanides are consistent only with an isocyanic constitution, and on this basis Nef’s additive hypo- thesis (3) gives a satisfactory account of their synthetic interactions ; the isocyanides are formed from silver cjanide by an additive process, however, and not by substitution.Finally, it is shown that a complete account of both classes of synthetic interactions of the metallic cyan- ides and of formonitrile is given by a modification of the additive hypothesis (4), according t o which addition to the carbon or nitrogen of the (6o)cyanogen radicle is dependent on the electrochemical conditions. The results may be summarised as follows : ,;r H*C(OH):NM -+ 4-f M+NC -+R.N:C (4) H*CiN f- M*N:CHCl +- M*N:C + M*NRI:C --f [HmN:C] +’ .% RI*N:CI*R -+ NIC*R Y, VI. The chemical, physical, and physiological properties of hydrogen cyanide accord with Gautier’s view of its identity with formonitrile, and although hydrogen isocyanide is still unknown, its absence and the intimate relation of its salts to the isomeric nitrile are explained by the modified additive hypothesis (4). +-1598 WADE : THE CONSTITUTION OF TEE METALLIC CYANIDES.I. The Synthetic Ifiteroctions of Potassium Cyanide. There are two fundamental methods of forming nitriles synthetically from potassium cyanide, namely, those of Pelouze and of Buckton and Hofmann mentioned above. With these may be included Merz's extension of the first method to aromatic sulphonates (Zsit. Chem., 1865,4, 33), and modifications of the second due to Gautier and others (imfm). It mill be convenient to discuss these groups separately. a. The Alkylsutphate Interactions. Method of Estimating Isocyanides and NitriZes.- Although all workers have experienced difficulty in preparing nitriles pure or in satisfactory quantity by the alkylsulphate method, and have inferred the presence of isocyanides from the disagreeable odour of the products, little attention has been paid to the conditions under which these impurities are formed ; there is I no record of any estimation of their amount, nor has their presence ever really been proved. As the boiling points of the respective isomerides are some 20' apart, it seemed feasible to separate them by fractional distillation, and the first experiments (Proc., 1900, 16, 156) appeared to justify this belief.The products obtained by distilling dry potassium methyl- or ethyl- sulphate with potassium cyanide separate cleanly into two nearly equal fractions when redistilled, and these have the odour and approximately the boiling points of the respective isomerides.On further ex- amination, however, it was found that although the higher or nitrilic fractions are homogeneous, the lower fractions are mixtures of constant boiling point, containing nitriles, alcohols, and hydrogen cyanide with comparatively little isocyanide. Mixtures of nitriles and alcohols of constant boiling point have been investigated by Gautier (loc. cit.) and Vincent and Delachanal (Compt. rend., 1880, 90, 747); they have minimum boiling points which are singularly steady over a wide range of composition, and when hydrogen cyanide and small quantities of isocyanides are added to them, products are obtained which are identical with the lower fractions from the synthetic interactions. These distil within two or three degrees of the pure isocyanides, and their odour is even more persistent, probably because the aloohol vapour modifies the paralysing action of the pure substances.It was not practicable, therefore, to separate the isocyanides as such (compare Browning, Trans., 1900, 77, 1236, and Kauffer and Pomeranz, Monatsh., 1901, 22, 492), and they were estimated by hydrolytic conversion into the corresponding amines, the hydrochlorides of which were separated from ammonium chloride by means of alcohol and ether, and weighed. The nitriles mere estimated roughly by con- version into the silver salts of the corresponding acids.WADE: THE CONSTITUTION OF THE METALLIC CYANIDES. 1599 Distillation of Dried Materials.-The materials were either thoroughly dried and sifted together or mixed with water, and were heated in an oil-bath.The action follows a well-defined course under each set of conditions, and with the dried materials is practically coincident with the fusion or softening of the alkylsulphate, the temperature varying from about 180' with potassium ethylsulphate * to 290' with the isoamyl compound; there is no charring, and the distillate is clear and practically colourless. It is particularly to be noted that there is no action until the mass becomes wet, so that the process is not a '' dry " one as is usually supposed, and as the liquid contains much alcohol from the decomposition of the alkylsulphate, the action takes place virtually in a saturated alcoholic solution. The estimated amounts of isocyanide in gram-mols.per gram-mol. of material * were : isocyanide in gram-mols. Me. Et. Pra. isoBu. isoAy. per gram-mol. ......... 0.024 0.043 0.022 0-014 nil. The maximum yield of isocyanide is thus 4.3 per cent. of that which is theoretically possible, The maximum yield of nitrile was 40 per cent. of the theoretical from the ethyl compound ; the amyl compound gave less than 15 per cent. DistilZation of Moistened Materials and of the Dry Residue therefrom.- When the materials are made into a cream with water, the latter alone passes over at first, but as soon as the mass becomes thick and pasty, effervescence and distillation set in, as when the materials are previously dried. The distillate separates into two layers, the heavier of which is mainly water, but the reaction otherwise follows the same course, the mass gradually drying up and distillation ceasing when the centre has become dry.On the other hand, the temperature is in every case much lower, the initial temperature of interaction varying from about 115' with potassium ethylsulphate t to 180' with the amyl compound, and the final temperature from about 130-250' in these extreme cases. The results obtained were as follows : Me. Et. Pra. isoBu. isoAy. isoCyanide in gram-mols. per gram-mol. ............ 0.031 0.050 0.020 0 010 trace The amount of isocyanide formed in saturated aqueous solution is therefore substantially the same as in the saturated alcoholic solution of the '' dry" reaction, the maximum being 5.0 per cent. of the * The reaction with the methyl compound requires a considerably higher temperature.t As Linneman (Amalen, 1868, 148, 252), working with very large quantities of potassium ethylsulphate, isolated triethylamine hydrochloride equivalent to 0.015 gram-mol., these figures are somewhat too high.1601, WADE : THE CONSTITUTION OF THE METALLIC CYANIDES. theoretical with the ethyl compound. Nitriles were present in some- *what smaller quantities than in the ‘‘ dry ” distillation. The main effect of adding water to the materials appears therefore in the lowering of the temperature of the interaction. An important difference becomes evident, however, if the heating of the residue be continued; no further sign of moisture or effervescence is apparent, but on reaching the temperature at which the interaction of the dried materials begins, a vigorous evolution of vapours takes place, which condense to a homogeneous distillate.The products formed a t this stage, the only one, i t is important t o note, in which no solvent is present, proved t o be essentially different from the others. Nitriles are still formed in considerable quantity, but isocyanides are entirely absent. b. The Aromatic Xulphonate Interactions. I n view of the material reduction of the temperature of interaction of the alkylsulphates in presence of water, the influence of this agent was tried on the distillation of potassium cyanide with potassium benzenesulphonate. The results in this case were negative, the only change observed being the steady hydrolysis of the potassium cyanide ; at temperatures near the softening point of soda-glass, however, benzonitrile is formed.c. The Alkyl Iodide Interactions. The Action in Alcol~olic Solution.-The alternative method for the synthesis of nitriles from potassium cyanide, by interaction with halogen compounds, was devised by Buckton and Hofmann (Zoc. cit.), at Williamson’s suggestion, for the preparation of propionitrile. It is not suitable for the preparation of pure nitriles on account of the tendency of these liquids to form mixtures of constant boiling point with the alcohol ; their presence ie demonstrated however, not only by the excellent yield of fatty acid obtainable, but by the identity of the products with alcoholic solutions of pure nitriles, and the possibility of isolating the latter from either (Gautier, loc.cit.) by a somewhat com- plicated process. There is no doubt, therefore, that the nitriles are present as such in the synthetic products, and are not combined with the alcohol as imino-ethers or the like. On the other hand, there is no evidence of the actual presence of isocyanides. Appreciable ‘quantities of the amines which would be produced by their hydrolysis are often present ; isopropylamine and diisopropylamine have been obtained in the preparation of isobutyro- nitrile (Siersch, Artnalen, 1868, 148, 263), and rz-butylamine in that of valeronitrile (Lieben and Rossi, Annulen, 1871, 158, 173). The presence of these bge-products is consistent with the initial formation of isocyanides, but it might equally well be due to the hydrolysis ofWADE: THE CONSTITUTION OF THE METALLIC CYANIDES.1601 alkyl isocyanates (Lieben and Rossi, Zoc. cit.), or the interaction of the alkyl halogen compounds with ammonia, formed by hydrolysis of the potassium cyanide (Frankland, Trans., 1880, 3'7, 567). To procure more decisive evidence, the various alkyl iodides were heated with potassium cyanide which was known to be free from cyanate, the amines being estimated as before. The pure cyanide was made by adding anhydrous hydrogen cyauide to the equivalent amount of alcoholic potash; the equivalent amount of alkyl iodide was then added, and the mixture boiled on a water-bath. The reactions with methyl and ethyl iodides are soon complete, and with propyl and iso- propyl iodides but little cyanide remains after 5 hours' boiling; with isobutyl and isoamyl iodides, however, the action is much slower, and even after 24 hours' boiling much material remains unchanged.The amounts of amine hydrochloride in gram-mols. per gram-mol. are appended (0.2 gram-mol. of material being used) ; the figures, as with the alkyl sulphates, are too high, analysis of the platinichlorides showing the presence of secondary or tertiary amines : Amines from interaction Me. Et. Pra. Prp. isoBu. isoAy. with alkyl iodides ... trace 0.005 0.032 0.038 0.018 0.023 The conditions of the experiments preclude the presence of alkyl cyanates, and the amines must therefore be formed either from iso- cyanides, or by interaction of the iodides with ammonia. Of the iodides used, however, the methyl and ethyl compounds interact with ammonia much more rapidly than the others, and it is scarcely conceivable that if the amines are due to this interaction, the methyl and ethyl amino- compounds should be formed in much the smallest quantity.Ammonia may be, and probably is, present, but it is in combination, the products being invariably acid,* and it is thus not in a state to react with the alkyl iodides. It will be seen later that isocyanides cannot exist in alcoholic solu- tion in presence of alkyl iodides, but are hydrolysed t o amine hydr- iodides, and there is no doubt therefore that the amines present in t h e synthetic products indicate the initial presence of these compounds. The Action in Absence of Alcohol.-In the absence of alcohol, the action between potassium cyanide and alkyl iodides is slow, and at 180°, the temperature recommended by Gautier (Zoc.cit.), is still in- complete after many hours. The best results are obtained at a some- what higher temperature, namely, 200' and upwards, and the product a t the end of 2 hours is then nearly pure nitrile. In neither case are isocyanides present as such, but after distilling the nitrile, a small, tarry residue is left, which yields the corresponding amine on hydro- * The acidity is apparently due t o the hydrolysis of the alkyl iodide. VOL. LXXXI. 5 P1602 WADE : TEE CONSTITUTION OF THE METALLlC CYANIDES. lysis; it is shown below that isocyanides are converted into similar tarry substances when heated with alkyl iodides, and the initial presence of the former may therefore be inferred.I n the search for more direct evidence, i t was found that the inter- action is dependent on the presence of water, and does not take place when the materials are dry. In one experiment, some ethyl iodide, which had been dried with fused calcium chloride for some days, was heated with potassium cyanide for 2 hours a t 200'; it distilled un- changed when the tube was opened, and the cyanide was also free from iodide ; the addition of a drop of water, however, secured the normal result. The interaction was then tried at various temperatures with moist ethyl iodide, and it was found that at 100' although little, if m y , propionitrile is formed, the unmistakable odour of etbyl isocyanide is apparent when the tube is opened ; the conversion into the tarry substance proceeds rapidly only at higher temperatures.It follows, therefore, that small quantities of isocyanides are actually formed in the interaction between alkyl iodides and potassium cyanide, but in the ordinary course are destroyed by hydrolysis or resinification. d. The Conditions Governing the Formation of the Isomerides. It is clear from the above results that the essential condition for the formation of isocyanides from potassium cyanide is the presence of a solvent. I n the alkylsulphate interactions, these substances only Occur when water or alcohol is present, and when these solvents are absent, as in the distillation of the dry residue from the moistened materials, no isocyanide is produced. I n the interaction with the benzenesulphonate, the conditions of temperature are such as to preclude the presence of a solvent, and no isocyanide is formed.With alkyl iodides in alcoholic solution, a solvent is again present, and the products of the decomposition of isocyanides are found, whilst when alcohol is absent water must be added before the reaction will take place. The conclusion, therefore, can scarcely be avoided that the interaction by which isocyanides are formed from potassium cyanide is ionic. Their pro- duction i n the alkylsulphate action can scarcely be due to ionic inter- change, because they are produced at one stage by decomposition of a dry solid ; ionic interaction is also obviously inadmissible with the sulphonates. On the other hand, the conditions of the alkyl iodide interactions are such as admit of their formation in this manner.Viewing the actions as a whole, however, it must be concluded that the nitriles are not produced in the same way as the iso- cyanides. As regards the nitriles, the question is more difficult.WADE: THE CONSTITUTION OF THE METALLIC CYANIDES. 1603 Before discussing further possibilities, it will be convenient to con- sider the conditions under which isocyanides are transformed into ni triles. IT. The Inadequacy of the E y p o t h e s i s of Isomeric Conversion. Although both Gautier and Hofmann (Zoc. cit.) observed small quantities of nitriles in isocyanides which had been prepared from silver cyanide, apparently due t o isomeric conversion, the former chemist failed to obtain evidence of such conversion with pure iso- cyanides. Weith,:however, showed (Ber., 1876, 9, 454) that phenyl isocyanide is transformed into benzonitrile at a high temperature, and, more recently, Nef has proved that o-tolyl and ethyl isocyanides (Annalen, 1892, 270, 311 ; 1894, 280, 295) undergo similar changes.The temperature at which the aromatic isocyanides are isomerised being far below that a t which the nitriles are formed in the interaction with sulphonates, i t appeared possible that the genesis of the latter is in these cases due to isomeric change. As regards the fatty nitriles, however, there appeared to be less warrant for this hypothesis; Geutier failed t o convert pure ethyl hocyanide a t ZOOo, and Nef specifically states that the temperature of the transformation is 230-255', and that the isocyanide remains unchanged after' heating for several hours a t 210°, a temperature well above that a t which the formation of the nitriles is complete in the synthetic interaction.T?be Conversioia of the Aliphatic isoCyanides.-In repeating and ex- tending the work of Gautier and Nef, the main question was one of temperature, and to secure definiteness and constancy in this respect, the isocyanides were heated in sealed tubes in the vapours of pure liquids, namely, nitrobenzene (208O), aniline (1 84'), bromobenzene ( 1 5 6 O ) , amyl alcohol (132O), and water. The amount of change was estimated by hydrolysing the product, and weighing the ammonium chloride and amine hydrochloride, which were formed from the nitrile and unchanged isocyanide respectively. The identity of the nitriles was confirmed by analysing the silver salts of the resulting fatty acids, The results a t first obtained were erratic, and it mas eventually found that when thoroughly dried with potash, both methyl and ethyl isocyanides are very resistant; in one case a specimen of the ethyl compound withstood a temperature of 250' for two hours, without undergoing appreciable change.If, however, the isocyanides are not too carefully dried, or the dry isocyanides are moistened with a drop of water, conversion is in every case effected as low as 184'. The nega- tive results of Gautier and Nef were thus due to the purity of their 5 P 21604 WADE : THE CONSTITUTION OF TEiE METALLIC CYANIDES. AcetonitriIe .................. Propionitrile ..............,n-Rutyronitrile ............ isoButyronitde ............ n-Baleronitrile.. ............. isoValeronitrile ............ isocapronit rile.. ............. materials. follows : The results with moist isocyanides may be summarised as 64.7 59-8 55 *6 55 -5 52.0 51.8 48.8 Temperature. Rate of change. 100' No change after many hours. 132 9 7 9 , 7, 156 Slight change with ethyl isocyanide, scarcely measurable. 184 Steady conversion in every case; 15-25 per cent. in 208 Rapid conversion, often practically complete in two four hours. hours. Analyses of Silver Salts. Gocyanide. Methyl .................. Ethyl ..................... n- Propyl .................. is.oPropy1 ............... isoButyl .................. iso Am y 1 .................. n-Rutyl .................. Percentage of silver in silver salt of acid.Nitrile. Found. Calculated. 64.7 59.7 55.4 55.4 51 '7 51 -7 48.0 The Conversion of Phenyl isoCyanide and Suggested Mechanism qt the Change.-The phenyl isocyanide which Weith converted into benzo- nitrile was made from chloroform and aniline by Hofmann's method (Proc. Roy. Soc., 1868, 16, 148), and contained much aniline, besides resinous and coloured substances ; such a product readily undergoes conversion in two o r three hours a t 230'. When, however, the isocyanide is purified by Nef's method (AnmaZen, 1892,270,274), it simply passes rapidly when heated into a solid resin, which is apparently identical with that which Nef has observed t o be formed slowly a t the ordin- ary temperature. This resin yields formic acid and aniline on hydro- lysis, but no ammonia or benzoic acid could be found, and the charac- teristic isocyanic grouping has therefore not undergone rearrangement of a nitrilic character.* When, however, aniline is added to the pure iso- cyanide, the isomeric conversion proceeds quite smoothly, and there is no difficulty in separating benzonitrile almost quantitatively from the product.It is thus clear that with phenyl isocyanide, as with the aliphatic * When treated with appropriate solvents, this resin yields a crystalline blue substance, which appears t o be the colouring matter of Hofmann's isocyanide.WADE: THE CONSTITUTION OF THE METALLIC CYANIDES. 1605 compounds, the transformation is not simple in character, and that inter- mediate products must be formed ; moreover in the case of the aromatic compound it seems probable that there is a stage which is analogous t o the Beckmann transformation of oximes.By the combination of phenyl isocyanide with aniline, a substance, diphenylformamidine, is readily formed, which yields benzonitrile a t a high temperature ; it is isomeric with a second substance, phenylbenzamidine, which is readily resolved into aniline and benzonitrile a t the temperature of the isomeric conversion. The first isomeride can be separated from the half-converted phenyl isocyanide without difficulty, and the presence of phenylbenzamidine is indicated by the ready manner in which the product a t this stage yields ammonia. The mechanism of the trans- formation may therefore be as follows : Diphenylformainidine.Pheny I benzamidine. Ph*CiN + NH,*Ph. The Inadequacy of Isomeric Conversion for the Genesis of Nit?-ih. The comparative slowness of the above isomeric change is in marked contrast with the rapidity with which, in the majority of cases, the nitriles are forued from potassium cyanide, and although tb0 temperature at which phenyl isocyanide is converted into benzo- nitrile is far below that which is required for the formation of the nitrile from potassium cyanide, the evident complexity of the trans- formation renders it unlikely that the isocyanide is formed as a pre- cursor. With the aliphatic compounds, the conditions of temperature are such as to render the hypothesis of isomeric transformation quite untenable. The conversion does not take place below 1 5 6 O , and even at 184' requires maoy hours, whereas the reaction with the dry ethylsulphate is complete in a few minutes a t a temperature of 180-190°.I n presence of water, moreover, acetonitrile and pro- pionitrile are formed freely below 130°, and Kaufler and Pomeranz (Zoc. cit.) have recently obtained the former compound in quantity from dimethpl sulphate and aqueous potassium cyanide at 0". Further evidence is afforded by the action of heat on the double salts which the isocyanides form with silver cyanide ; these solids de- compose cleanly into their constituents a t a temperature of 190-200°, or substan tially that at which the corresponding nitriles are formed from potassium cyanide in the '6 dry" reactions ; yet the isocyanides thus produced contain only traces of uitriles.It is obvious, therefore, that1606 WADE : THE CONSTITUTION OF THE METALLIC CYANIDES. only a very small proportion of the nitriles formed from potassium cyanide can be attributed to isomeric change. The hypothesis of isomeric transformation does not adeqiiately account for the formation of the aliphatic nitriles from pottssium cyanide, and i t is doubtfu whether it represents the formation of benzonitrile. 111. The Inadequacy of the Hypothesis of Tautomerisin. The isocyanides and nitriles being independent products, it follows that if they are both formed by ordinary interchange of radicles, potassium cyanide must be a mixture i n which the nitrilic form pre- ponderates. It is important to note that the evidence for the nitrilic constitution of the alkali cyanides is based exclusively on the produc- tion of nitriles from them.I n every other respect, their behaviour is anaIogous t o that of the nlkyl isocyanides. Their solutions dissolve silver cyanide just as the alkyl isocyanides do, and from these solutions in each case double salts can be separated of the form RAg(CN),. Potassium cyanide combines with ethyl hypochlorite in the same way as ethyl isocyanide does (Nef, Annalen, 1895, 28’7, 274). Tetramethyl- ammonium cyanide, which is formed by the combination of the alkali hydroxide with the acid, and resembles the alkali cyanides, decomposes into trimethylamine and methyl isocyanide when heated (Thompson, Ber., 1883, 16, 2338). The general properties of the alkali cyanides are in sharp contradiction to the alleged nitrilic character deduced from their synthetical interactions.With the cyanides of the heavy metals, the synthetical actions are themselves mutually contradictory. When alkyl cyanides are made from silver cyanide a t a sufficiently low temperature (Gautier, Eoc. cit.), a practically quantitative yield of isocyanide is obtained, free from a trace of nitrile; the present writer has examined for nitriles many specimens prepared in this way, with entirely negative results. On the hypothesis of direct interchange, silver cyanide is thus exclusively isocyanic. Yet with acyl compounds, such as benzoyl chloride (Liebig and Wohler, AnmaZen, 1832,3,267) and acetyl chloride (Hubner, ibid., 1861, 120, 334), large yields of acyl cyanides are obtained which are undoubtedly nitriles, for they are converted by hydrochloric acid into the corresponding amides (Claieen and Shadwell, Ber., 1878, 11, 1563).On the hypothesis of direct interchange, silver cyanide is thus nitrilic. This conclusion cannot be explained by the tautomerism of hydrogen cyanide ; it is obviously impossible to assume that the acid from which the silver salt is prepared is a nitrile when the salt is intended for interaction with acetyl chloride, but an isocynnide when it is to beWADE: THE CONSTITUTION OF THE METALLIC CYANIDES. 160'7 used for the preparation of ethyl isocyanide. I f direct interchange of radicles be assumed, it follows that the silver salt is itself tautomeric ; Laar's hypothesis, however, is based on the lightness and high velocity of the hydrogen atom, and its extension to the heavy silver atom is not justifiable dynamically; an atom cannot vibrate in a stable condition around a group of one-fourth of its mass.Apart from the synthetical interactions with acyl chlorides, there is no more reason for assuming a nitrilic constitution for silver cyanide than for the potassium salt. The same is true of the cyanides of the other heavy metals ; mercuric cyanide also yields both isocyanides and nitriles under similar conditions, yet is undoubtedly an isocyanide, its low electrolytic conductivity (Ley and Kissel, Ber., 1899, 32, 1357) and the low E.N.F. of its couple with mercury (Kieseritzky, Zeit. physikal. Chem., 1899,28, 3S6j both pointing to a linking of mercury with nitrogen.The evidence of the synthetic interactions being contradictory and the other chemicaI actions of the salts pointing exclusively in one direction, it must be concluded that the metallic cyanides are simple substances analogous to the isocyanides in constitution, and that the direct interchange of radicles plays an insignificant part in their synthetic actions. IV. The Additive Hypothesie. Its primary assump- tion is based on t h e fact that the activity of the alkyl isocyanides is caused by the unsaturated, bivalent condition of the carbon; ethyl and phenyl isocyanides, for example, combine with acetyl and similar chlorides, forming the alkyliminochlorides of pyruvic and other ketonic acids, the acyl chloride becoming linked directly to the carbon (Nef, Annalen, 1892, 270, 295) : Et*N:C + AcCl = Et*N:CCl*Ac (or CH,*CO*CCI:NEt).The phenyl compound is much less active than the methyl com- pound in forming such combinations, and Nef explains this by ttssuming that the additive power of the isocyanogen carbon is de- zreased by tbe juxtaposition of negative, and increased by that of positive, radicles. As potassium isocyanide contains a highly Dositive radicle, i t should therefore form additive compounds very "eadily, and the compounds with alkyl iodides and the like may be 3xpected t o break up, leaving nitriles : The only remaining hypothesis is that of Nef, K*N:C + EtI = E*N:CI*Et = KI + NiOEt. The E'ormation of Nitriles from Potassium and Silver Cyanides.-The rarious phases of the interactioo of potassium cyanide, as described1608 WADE : TRE CONSTITUTION OF THE METALLIC CYANIDES.above, are satisfactorily accounted for by this hypothesis. Direct interchange of radicles only occurs when the:conditions favour ionisation, as should be the case, and the limited yield of isocyanides thus obtained is intelligible on the assumption that the additive compounds are incapable of breaking up again into their original constituents, and withdraw the cyanogen ions from solution, . The cessation of the inter- action with potassium alkylsulphates when the mass becomes dry and the decomposition of the dry residue a t a higher temperature dis- tinctly point to the presence of such moderately stable intermediate compounds. As regards the synthetic interactions of the alkali cyanides, Nef's hypothesis, although not absolutely proven, gives an accurate repre- sentation of the facts, and the actions may therefore be represented as follows : .. K*NC + EtKS04 = KKSO, + Et-NC; E*N:C + Et*KSO, = K*N:C(SO,K)*Et = K,SO, + NiC'Et; K*N:C + Ph*SO,'I( = T(.N:C(SO,K)*Ph = K&O3 + NiC'Ph; K*N:C + Ac,O = K*N:C(OAc)*Ac = KOAC + NiC*Ac. The formation of acyl cyanides from the silver salt is accounted for in the same may, and the parallel to the corresponding actions with isocyanides is so close as to leave no doubt as to the correctness of the explanation : Et*N:C + AcCl = Et*N:CCl*Ac (-+ EtONH, + CO,H*Ac) ; Ag*N:C + AcCl = Ag*N:CCl*Ac = AgCl + NiC*Ac (-+ CO,H*Ac). The Formation of isoCyanides from Silver Cyanide.-Nef's hypothesis does not explain, however, the formation of isocyanides from the cyanides of the heavy metals, of which silver cyanide may be taken as the extreme type.On account of the apparent absence of definite action between the alkyl iodides and alkyl isocyanides, Nef concludes that there is no parallelism in this respect between the isocysnides and silver cyanide, and that the only method by which the isocyanides can be formed from the latter is that of direct replacement (ausschliesslich directe Emetxung) of the metal by an alkyl group. This assumption is not warranted by the facts. Silver cyanide is not appreciably ionisable, and there is obviously an additive stage in Gautier's ;reaction. When dry silver cyanide is boiled with methyl iodide on a water-bath, the iodide is rapidly absorbed, even when the amount of silver salt is insuffi- cient to form the double silver alkyl compound; the product is a viscous liquid which solidifies on cooling, and does not yield isocyanide unless heated a t 180-200' or treated with aqueous potassium cyanide a t 100'.There is little doubt that the initial stage of thisWADE: THE CONSTITUTION OF THE METALLIC CYANIDES. 1609 action is parallel t o the action of alkyl iodides on isocyanides, just as the initial stages of the action of acyl chlorides on these compounds are similar. The Action of AllEyZ Iodides om isoCyanides.-The action of alkyl iodides on isocyanides was first studied by Gautier (Zoc. cit.), who expected to obtain a crystalline ‘( carbylammonium ” iodide, CH,*NMeI:C; he found only an unworkable tar, which, however, resembled ammonium salts in being soluble in water, although its con- stituents are insoluble.Liubawin (J. Russ. Phys. Chem. Soc., 1885, 1, 193) repeated this work and obtained both methylamine and dimethylamine by heating the t a r with baryta; he also prepared a similar t a r from ethyl isocyanide and ethyl iodide. Nef has more recently obtained a similar tar from phenyl isocyanide. The present writer finds that the interaction is general, and has obtained similar products from all the isocyanides available ; unfortunately, they have proved equally unworkable, so that complete analysis is impracticable. It is most probable, however, that these tars, whilst mainly polymerised forms of the isocyanides, consist in part of additive compounds of the type formulated by Gautier, and there is no doubt of the presence in them of compounds in which nitrogen is linked to two alkyl radicles.On hydrolysis, they yield primary amines, which contain a considerable proportion of the secondary or tertiary bases, as the following analyses of the platini- chlorides show : MeNC,MeI. Pt found = 41.03 per cent. = 11 per cent. of NHMe, ; EtNC,MeI ,, ,, 38-59 ,, ,, 10 ,, ,, NHEtMe. (NH2Me),,H2PtCI, requires 41.30, (NH,Et),,H,PtCl, 38.98 per cent. When the action is carried out in alcoholic solution, preferably in sealed tubes at looo, much more definite results are obtained. The isocyanide completely disappears in the course of a few hours, and on evaporating the product, tars are left which readily crystallise ; in some cases, crystals were formed before the tube was opened.The products are higbly coloured, but after washing with, or recrystaliising from, chloroform, they form colourless plates which have all the characters of amine hydriodides, and resemble specimens of the latter prepared directly from the respective amines. The appended analyses show that in every case considerable proportions of secondary or tertiary bases are also present, the carbon being too high, and the iodine too low. The nitrogen was determined by distilling with alkali and titrating the amine, the iodine by Volhard’s, and in some cases, X, by Carius’s method.1610 WADE : THE CONSTITUTION OF THE METALLIC CYANIDES. Products of the Action, of AZkgZ Iodides on isoCyunides. Iodide. Methyl .................isoPropy1 ............... isoAmyl ................. , , ................. Ethyl ..................... ,) ............... CH3*NH,, H I ...... Methyl .................. Ethyl ..................... n-Propyl .................. ,, .................. n-Butyl .................. C,H,.NH,,HI ... Me thy1 .................. ,) .................. C,Hv*NH,,HI ... Me thy1 .................. Ethyl .................... C4H9-NH,, HI ... Methyl .................. Ethyl .................... C,H,,*NH,,HI ... M. p. I C. I H. Met?$ isocyanide. 240-250" 2 4 5-250 - 244-248 - 247-249 249 . 8-9 1 8 - 5 8.8 8 .O 8 '3 I 8.5 ~ 7.5 Ethyl isocyanide. 183-186" 183-185 183-1 85 182-185 - 187 14.2 15.0 15.8 15'0 15.4 13 *9 4.0 4 '4 3-6 3 '9 3.9 3.8 - 4-8 4-6 4 '9 4'7 4'7 4.6 n- Propyl isocyanide.- 19.8 5'3 - - n-Butyl isocyanide. - 25.3 6 2 - 1 . 24'0 I 6.2 - 23.9 6.0 isoArnyZ isocyanide. 29.0 6.7 N. I. 77.8 78-2 X 77.2 78'4 78'3 x 79.8. - 72.6 72 '2 71.9 72.0 73.4 - 65 -2 65.8 X 67-8 , - 6 2 5 X 63 .I 57.5 x 59.0 - Similar products were obtained from isopropyl, isobutyl, allyl, and phenyl isocyan- These hydriodides are formed by direct hydrolysis of the isocyanides or their additive products, the necessary water being abstracted from the (anhydrous) alcohol; ether is separable i n quantity, nnd the presence of an alkyl formate was also proved. The action may be compared with the dehydration of acetic acid by ethyl isocyanide (Gautier, Zoc. cit.), and the dehydration of sulphuric acid by potassium cyanide (Wade and Panting, Trans., 1898, '73, 258) : ides, but were not analysed. Et*N:C1 + EtI + 4EtOH = Et*NH,,HI + H*CO,Et + 2Et20; Eb*NEtI:C + 3EtOH = NHEt,,HI + H*CO,Et + Et,O; Et*N:C + ZACOH = Et*N:CH*OH (=H*CO*NHEt) + Ac,O.WADE : THE CONSTITUTION To prove that addition had isocyanide, the products, both examined for fatty acids other negative results.OF THE METALLIC CYANIDES. 1611 not been made to the carbon of the solid and liquid, were in many cases than formic acid, but with uniformly Froposed Modification of the Additive Hypothesis. -The nitrogen alone of the isocyanide being thus affected, there are two available modes of action of alkyl iodides on isocyanides; the isoeyanide may become polymerised, or i t may form an additive compound with the iodide. With silver cyanide, the second course is alone possible, and additive compounds are formed in which the alkyl iodide is linked to the nitrogen, aod which break up into silver iodide and the Et*N:C + Me1 = Et*NMeI:C; Ag*N:C + Me1 = Ag*NMeT:C = AgI + NMe:C.The mechanism of the formation of isocyanides from silver cyanide is thus comparable with that of the action by which acetyl cyanide is formed, in the one case the new group becoming linked to the nitrogen, and in the other to the carbon. At the same time, no explanation is afforded of this essential difference in detail; there is no apparent reason why addition should not be made to the nitrogen when alkyl but to the carbon when acyl mtdicles are interacting, and it is in t h i s respect that the additive hypothesis needs carrying to its logical conclusion.The only difference between the two sets of reactions is that which exists between the alkyl and acyl compounds themselves, and it is to this that the difference in the additive power of the silver cyanide must be due : . alkyl isocyanides : * Ag*N:C + EtI = Ag*NEtI:C = AgI + NEt:C; Ag*N:C + AcCl = Ag*N:CClAc = AgCl + N:C*Ac. Comparing these interactions with the ;parallel actions with alkyl .isocyanides : Et*N:C + EtI = Et*NEtI:C; Et*N:C + Ad21 = Et*N:CClAC; i t will be seen that, in both cases, it is the strongly negative acid radicle which combines with the carbon, and the feebly positive alkyl which combines with the nitrogen; when, on the other hand, the radicle of the isocyanide is itself strongly positive, as i n potassium cyanide, the alkyl and acyl radicles alike combine with the carbon.* Kaufler and Ponieranz (Em. cit.) regard the metallic cyanides as nitriles, and conclude that the synthetical nitriles are formed from these by ionic interaction (KCN + Me1 = KI + MeCN), and the isocyanides by means of additive compounds of the type Ag'CiN:MeI. + - -I--161 2 WADE : THE CONSTITUTION OF THE METALLIC CYANIDES. The additive power of the carbon atom of the isocyanide radicle is therefore dependent, not merely on the electrochemical character of the metallic or alkyl radicle of the cyanide itself, as Nef assumes, but on its electrochemicalposition velatively to the radicle of the inter- acting alkyl compound: it is only when the isocyanide radicle is sufficiently positive with regard Lo the radicle of the interacting molecule that the latter combines with the carbon of the isocyanogen group, and when these radicles are electrochemically adjacent, the interacting molecule combines with the nitrogen.With this extension, the additive hypothesis gives a complete account of the synthetical interactions : K*N:C + EtI = K*N:CEtI = KI + NiC*Et K*N:C + EtKSO, = K*N:CEt*SO,K = K,SO, + NiC*Et. + + strongly feebly Et*N:C + EtI = Et*NEtI:C Ag*N:C+ E t I = Ag*NEtI:C = AgI + NEt:C + -I- feebly feebly r feebly strongly i i Et*N:C + AcCl = Et*N:CCIAc Ag*N:C+ AcCl = Ag*N:CCIAc = AgCl + NiC*Ac - + The modified hypothesis also accounts for the formation of nitriles in the diazo-synthesis ; the diazo-chlorides, being strongly negative, combine with the carbon of the cuprous or other cyanide, forming com- pounds of the same type a s those which are formulated above; these decompose into metallic chlorides and the diazo-cyanides, which (Hantzsch and Schultze, Ber., 1895, 28, 666) are the precursors of the nitriles : Cu*N:C + Ph*N,*Cl= Cu*N:CC1*N2*Ph = CuCl i- NiC*N2*Ph.* - + feebly strongly it The hypothesis is applicable to other groups of reactions, in which the con- stitution of a metallic salt is deduced from its interactions with alkyl compounds.It does not follow, for example, that because silver cyanate and nitrite yield alkyl isocyanates and nitro-compounds respectively, the metal is necessarily linked t o nitrogen ; it may equally well be linked t o oxygen, the alkyl derivatives being formed by means of additive compounds : Ag'O*N:O + Me1 =Ag'O*NMeI:O =AgI + 0:NMe:O ; Ag'O'CiN+ MeI=Ag'O'CI:NMe=AgI +O:C:NMe.WADE: THE CONSTITUTION OF THE METALLIC CYANIDES.1613 V. C o n s t i t u t i o n of H y d r o g e n Cyanide. It has been implicitly assumed that, by establishing the constitution of the metallic cyanides, that of the hydrogen compound would be fixed, and hydrogen cyanide has accordingly been regarded as a nitrile or an isocyanide, as the metallic salts were assigned to one or the other of these classes. The complexity of the relations between the metallic and alkyl cyanides renders this assumption untenable; i t no more follows that hydrogen cyanide is an isocyanide because it is intercon- vertible with silver cyanide, than that the latter is a nitrile because it is interconvertible with acetyl cyanide.The methods available for the solution of this problem are a comparison of the reactions of hydrogen cyanide with those of its alkyl derivatives, and a similar comparison of i t s physical properties. The Chemical Relutions of Hydrogen Cpaide.--The method of hydrolysis, which gives the decisive data for the constitution of the alkyl cyanides, a t first sight appears to furnish none for that of the hydrogen compound ; whether the latter be formonitrile or hydrogen isocyanide, the same products will be formed : HI-CiN 4 H*CO,H + NH, +-= 0:N.H. When, however, the actual details of the hydrolysis are considered, it is clear that hydrogen cyanide belongs essentially t o the former class. It is readily decomposed by boiling alkalis in the same way as nitriles, whereas isocyanides are absolutely unaffected by these agents, and whilst the isocyanides are rapidly and violently decom- posed by the mineral acids, hydrogen cyanide, like acetonitrile, for example, is hydrolysed by them comparatively slowly.Perhaps the most decisive evidence agaiqst an isocyanic. constitution is furnished by the behaviour of the acid with silver cyanide. One of the most striking properties of the isocyanides, which they share with the alkali cyanides, is their power of combining with this salt, which they dissolve with great rapidity t o a clear solution a t the ordinary temperature, much heat being developed. Nitriles are devoid of this solvent action, and hydrogen cyanide resembles them precisely. Experiments in which various quantities of the anhydrous acid were boiled with silver cyanide gave uniformly negative results, even 100 C.C.thus saturated leaving no appreciable residue on evaporation. Hydrogen cyanide thus differs radically from the isocyanides in two of their most characteristic properties, and in these very respects behaves precisely as the nitriles. Negative evidence i n favour of a nitrilic constitution is furnishad16 14 WADE : THE COXSTITUTION OF THE METALLIC CYANIDES. by the action of heat on the acid. If it be t h e first of the isosyanides, it should undergo transformation into the corresponding nitrile when heated, but no evidence exists, or could be obtained, of the formation of such a compound. Dry hydrogen cyanide is perfectly stable at the ordinary temperature, as Gautier showed (Zoc.cit.), but at looo, or at the ordinary temperature in presence of potassium cyanide, it is slowly converted into a hard, black, amorphous mass, from which a termolecular polymeride is extracted by ether (Lescaur and Rigaut, Compt. rend., 1879, 89, 310). This polymeride yields glycosine when hydrolysed, and hence is aminomalononitrile, NH,*CH(CiN), ; its formaticn points to the polymerisation of formonitrile, and not of hydrogen isocyanide, for nitriles always polymerise by the linking of the cyanogen carbon ; bimolecular acetonitrile, for example, is iminobutyroni trile, CH,*C( :NH)*CH,*CN, If hydrogen cyanide is identical with formonitrile, this polymeric change is intelligible, but if i t be an isocyanide, a preliminary isomeric conversion must be assumed, some indication of which should be obtainable during the slow formation of the polymeride.I n a series of experiments, in which the anhydrous or nearly anhydrous acid was heated at temperatures ranging from 50° t o 200°, no indication of such a n isomeride was apparent ; the liquid part of the product consisted throughout of unchanged hydrogen cyanide distilling sharply at its original boiling point. The existence of a liquid isomeride of higher boiling point, such as Nef suggests (Amnalen, 1892, 270, 329), is thus negatived. Hydrogen isocyanide would have very different properties. It would be an extremely active substance having a boiling point con- siderably below that of the nitriles, mould readily dissolve and com- bine with silver cyanide, would interact explosively with hydrochloric acid, azld would form additive compounds analogous to those of the alkyl isocyanides.Most of the chemical aitions of hydrogen cyanide point, in fact, to a nitrilic constitution. Its production when formnmitle is dehydrated with phosphoric oxide (Hofmann, Trans., 1863,16,74), and the similar decomposition of formoxime (Dunstan and Bossi, ibid., 1898, 73, 360) are parallel t o the formation of the nitriles from the homologous amides and aldoximes. Its additive compounds are of the same type as those which are formed by the nitriles ; the compounds with stannic chloride, ZHCN,SnCl,, antimonic chloride, 3HCN,SbCl, (Klein, Amnalen, 1850, 74, 86), and cuprous chloride, HCN,2CuC1,2HCl (Rabaut, Bull. Soc. Chim., 1898, [iii], 19, 785) may be instanced. isocyanides do not form additive compounds of this type.The union of hydrogen cyanide with diazomethane t o form aceto- nitrile (Pechmann, Be?.., 1895, 28, 857), and with acetic acid t o formWADE: THE CONSTITUTIOX OF TEE METALLIC CYANIDES. 1615 acetylformamide, point t o the same conclusion ; isocyanides dehydrate acetic3 acid, forming alkylformamides (compare p. 1610). The stability of bydrogencyanide towards ethyl hypochlorite and chlorine at - 15' (Nef, Annalen, 1895,287, 274) is inmarked contrast with the activity of ethyl isocyanide with these agents at the same temperature. There is, in fact, no chemical evidence in favour of an isocyanic constitution (except that which involves the assumption of substitution), and much which directly indicates a nitrilic constitution.Physical Properties of Hydroyen Cyanide.-Recent measurements of the physical constants of hydrogen cyanide point even more decisively to the same conclusion. Briihl (Zeit. physikal. Chem., 1895, 16, 512) has shown that its molecular refractivity agrees with that of a nitrile, and is much lower than that calculated for an isocyanide of this composition. Schlundt (J. Physical Chem., 1901, 5, 157) has shown that its dielectric constant is exceedingly high, as would be expected from tho high constants of the lower nitriles; Centnerszwer (Zeit. plqsikal. Chem., 1901, 22, 218) has shown thatits ionising power for potassium iodide is similarly very great. The values of the electrical constants for the isocyanides are unknown, but from some rough comparative measurements with methyl isocyanide the writer finds that its dissociiktive power is far less than that of acetonitrile.The most important physical evidence against the nitrilic constitu- tion of hydrogen cyanide is its low dissociation constant, from which Ostwald has concluded (Lehrbuch, 1887, ii, 849) that i t cannot contain the strongly negative normal cyanogen radicle; it may be pointed out, however, that the trichloromethyl radicle, CCI,, is much more negative than the cyano-group, and when introduced into formic acid increases its acidity enormously," yet its hydrogen compound, chloroform, is not an acid at all. Physiological Properties of Hydyogen Cyanide.-The intensely poisonous character of prussic acid has often been cited as evidence of an isocyanic constitution, the Gocyanides being assumed to be highly poisonous, and the nitriles innocuous. The reverse is nearer the truth, however ; recent physiological work (Lang, Arch.exp. Path. Pharm., 1894, 34, 247; Verbrugge, Arch. Phamnacodynam., 1898, 5, 181) has established that the aliphatic nitriles, and cyanogen itself, produce all the symptoms which are characteristic of prussic acid poisoning- spasmodic respiration, accelerated heart-beat, muscular paralysis, dim- inished oxidation, and lowered body temperature. The physiological properties of the isocyanides have not been studied with the same degree of accuracy, but are quite different from those of hydrogen cyanide. Qautier (Zoo. cit.) injected methyl isocyanide * K, (formic acid) = 0'0214 ; K2 (trichloracetic acid) = 120.1616 WADE : THE CONSTITUTION OF THE METALLIC CYANIDES.into rabbits without producing toxic symptoms, but found that con- tinuous work with these substances produces ill-health, and the experience of the present writer and others working in the same laboratory confirms the latter statement ; the isocyanide vapours interfere with the digestive systemand produce symptoms akin to those of jaundice. The author has also noticed the important difference that whilst the system soon learns to tolerate hydrogen cyanide vapour to a surprising degree, it eventually becomes very sensitive to isocyanides. Another point of distinction between hydrogen cyanide and the isocyanides is that the vapour of the former, although very harsh and disagreeable in odour (or, more correctly, in taste), is devoid of the peculiarly nauseous bitterness which is characteristic of the isocyanides.The Belation of Pownonitrile to the Metallic Cyanides.-Whilst the evidence for the isocyanic constitution of the metallic cyanides is thus conclusive, there are no grounds for assigning this constitution to the hydrogen compound ; its reactions and physical and physiological properties alike indicate its identity with formonitrile. The metallic cyanides, as Gautier pointed out more than 30 years ago, are salts of the unknown hydrogen isocyanide, H*N:C. The undeveloped state of structural chemistry at t h e time of Gautier's work precluded the explanation which is now possible of the relation of formonitrile to the salts of this labile isomeride.The convertibility of the metallic cyanides into formonitrile by treatment with acids follows at once from the modified electrochemical hypothesis by which the synthetic interactions are explained. All acids necessarily contain electro-negative radicles, and therefore combine with the carbon of the metallic cyanides (compare p. 1612), whatever the metal may be; the additive compounds thus formed necessarily break up into formonitrile and the metallic salt of the acid, just as the alkyl compounds yield the homologous nitriles : K*N:C + HCI = K*N:CHCl = KC1 + NiCH; K*N:C + EtCl = K*N:CEtCl = KCI + NiCEt. Any hydrogen isocyanide which may be formed by ionic interchange will either be hydrolysed at once by the acid in the manner charac- teristic of isocyanides, or converted into the stable nitrilic form : H*N:C + HCI = H*N:C'HCl = HCl + NIGH.There is no other way of preparing hydrogen cyanide from metallic cyanides, and it is thus impossible that the labile isomeride can remain. The reverse conversion of formonitrile into the metallic isocyanides is parallel to that of the nitromethanes into salts of the isonitro-WADE : THE CONSTITUT~ON OF THE METALLIC CYANIDES. 1617 methanes. The nitromethanes, like formonitrile, are inert compounds of scarcely appreciable acidity, but they combine with alkalis in the same manner, forming salts of the labile iso-compounds; the corre- spondence is complete, and the acid isonitromethanes have been iso- lated (Hantzsch, Ber., 1896, 29, 699; 1899, 32, 607) : CH,.NO, + KOH = CH,*NO(OH)*OK = H,O + CH,:NO*OK; H*CiN + KOH = H*C(OH):NK = H,O + C:NK.The assumption that the metal combines with the nitrogen of the nitrilic group is justified by the recent work of Blaise (Conpt. rend., 1901, 132, 38, et Seq.) on the interaction of nitriles with magnesium alkyl haloids. I n these actions, additive compounds are formed in which the alkyl group combines with the carbon of the cyanogen, and the metal with the nitrogen; the reaction has been stxidied with all classes of nitriles, and there is no exception t o the rule : R*CiN + Mg1.R = R*CR:N*MgI (+H,O -+ RG0.R). VI. The Interactions of Formonitrile and the Metallic iso- Cyanides as represented b y the Modi$ed A d d i t i v e Hypothesis. The sole evidence for a nitrilic constitution for the metallic cyanides, namely, the formation of nitriles from them by synthetical processes, is equally well explained by the hypothesis of additive compounds, analogous to those which are known to be formed by the alkyl iso- cyanides ; the synthetical formation of the isocyanides is explained in the same way, the addition being made to the carbon or nitrogen atom of the cyanogen radicle, according to the electrochemical conditions ; the interconvertibility of the metallic cyanides and formonitrile is also accounted for by this hypothesis.Until the additive compounds and hydrogen isocyanide are isolated, i t must necessarily remain an hypo- thesis; it is, however, the only one which accounts for all the facts, and is therefore entitled to supersede its defective precursors. CHEMICAL DEPARTMENT, GUY'S HOSPITAL, LONDON BRIDGE, S.E. VOL. LXXX1. 5 QWADE : THE CONSTITUT~ON OF THE METALLIC CYANIDES. 1617 methanes. The nitromethanes, like formonitrile, are inert compounds of scarcely appreciable acidity, but they combine with alkalis in the same manner, forming salts of the labile iso-compounds; the corre- spondence is complete, and the acid isonitromethanes have been iso- lated (Hantzsch, Ber., 1896, 29, 699; 1899, 32, 607) : CH,.NO, + KOH = CH,*NO(OH)*OK = H,O + CH,:NO*OK; H*CiN + KOH = H*C(OH):NK = H,O + C:NK. The assumption that the metal combines with the nitrogen of the nitrilic group is justified by the recent work of Blaise (Conpt. rend., 1901, 132, 38, et Seq.) on the interaction of nitriles with magnesium alkyl haloids. I n these actions, additive compounds are formed in which the alkyl group combines with the carbon of the cyanogen, and the metal with the nitrogen; the reaction has been stxidied with all classes of nitriles, and there is no exception t o the rule : R*CiN + Mg1.R = R*CR:N*MgI (+H,O -+ RG0.R). VI. The Interactions of Formonitrile and the Metallic iso- Cyanides as represented b y the Modi$ed A d d i t i v e Hypothesis. The sole evidence for a nitrilic constitution for the metallic cyanides, namely, the formation of nitriles from them by synthetical processes, is equally well explained by the hypothesis of additive compounds, analogous to those which are known to be formed by the alkyl iso- cyanides ; the synthetical formation of the isocyanides is explained in the same way, the addition being made to the carbon or nitrogen atom of the cyanogen radicle, according to the electrochemical conditions ; the interconvertibility of the metallic cyanides and formonitrile is also accounted for by this hypothesis. Until the additive compounds and hydrogen isocyanide are isolated, i t must necessarily remain an hypo- thesis; it is, however, the only one which accounts for all the facts, and is therefore entitled to supersede its defective precursors. CHEMICAL DEPARTMENT, GUY'S HOSPITAL, LONDON BRIDGE, S.E. VOL. LXXX1. 5 Q

ISSN:0368-1645    

DOI:10.1039/CT9028101596

出版商:RSC    

年代:1902

数据来源: RSC

摘要:

INDEX OF AUTHORS’ NAMES. TRANSACTIONS. 1902. (Marked T.) ; and to Proceedings, 1901-1903; Nos. 241 to 258, Nov., 1901 -Dee., 1902 (marked P.). COMPILED BY MARGARET D. DOUGAL. A. Allen, Cluwles. See Eobcrt Howsoit Pickard. Allison, John Amptoncl. See Arthur George Perkin. Anderson, W. 12. See Joseph TVdliam Mellor. Angel, Andrea, and A ~ g ~ s l i ~ George Vernon Harcourt, observations on the phenomena and products of decom- position when normal cupric acetate is heated, T., 1385 ; P., 1902, 185. Armstrong, Henry Edward, Frankland memorial lecture, P., 1901, 193. Armstrong, Henry Edward, and Edward Horton, the part played by residual affinity in the formation of substitution derivatives ; the orienting iufluence of sulphur, P., 1901, 246. Armstrong, Henry Edmwd, and Thontm Xartiit Lowry, stnclies of the terpenes and allied compounds ; the sulphonw- tion of camphor.I. Camphorsul- phonic acid (Reychler) ; the formation of nnhydramides, T., 1441; P. 1901, 182. -- studies of the terpenes and allied conipounds ; the sulphonation of camphor. 11. 8-Bromocamphor and its tlerivatives ; 8-bromocamphoric acid, T., 1462; P., 1901, 217, 244. -- - studies of the terpcnes and allied compounds ; the sulphonation of camphor. 111. The optical inver- sion of camphor and the mechanism of hetero- and meso-sulphonation, and of homo- arid hetero-brornination, and of dehydration, T., 1469. See John 2’lLcodore Hewitt. LXXSI. Auld, XanLucZ James X m w u ~ t . B. Baker, Berbert Brercton, the union of hydrogen and oxygen, T., 400; P., 1902, 40. Baker, Jtclian Levelt, the action of un- germinated barley diastase on starch.Part I., T., 1177; P., 1902, 134; discnssion, P., 135. Ball, Wulter C‘raven, a new colour re- action of hydroxylamine, p., 1902, 9. Baly, Edward Clmrles Cyril, and Bredcrick George Donnan, the variation with temperature of the surface energies and densities of liquid oxygen, nitro- gen, argon, and carbon monoxide, T., 907 ; P., 1902, 115. Bassett, Bcitry, j z ~ i b . See Frederick Gcorp Donnan. Berthelo t, J1ai*cellix [Pierre Zz~gkm], coiigatnlatorg address to, P., 1901,250. Bone, TVzlhin A.r.thitr, and Charles Hewy Gralinm Sprankling, the synthesis of alkyl tricarball y lic acids, T., 29 ; P., 1901, 215. -- the brominntioii of trimethyl- succiiiic acidand tlie interactionofethy- bromotrimethylsuccinate and ethyl sodiocyanoacetate,T.,50 ; P, ,1901,243.Bone, William Arthur, and Richard V. Wheeler, the slow oxidation of meth- ane a t low temperatures, T., 535 ; P., 1902, 51. Bowdler, William Azcdley. See Xobert Hotuson Pickard. Bradley, Sirhey Wallace. See JoIi I L Y’Ii eoclore Hewit t. Brauner, BoAicsZnv, and Frnpntiiek PavliEek, revision of the atomic weight of lanthanum, T., 1243 ; P., 1901, 63. 5 R1620 lNDEX OF AUTHORS. Briggs, Xa?,~ucE Hcnrg Cliford, a series of double chroniates, P., 1902, 254. Briggs, Samuel Henry Cli$ord. See also Julius Beremi Cohen, and Arthzu George Perkin. Brown, Adrian John, enzyme action, T., 373 ; P., 1902, 41. Brown, Horace T., and Tom AIdrich Glendinning, the velocity of hydro- lysis of starch by diastase, with some remarks on enzyme action, T., 388; P., 1902, 43.Browning, Kendull Colin, phosphorus suboxide, P., 1901, 243. Burkard, Emil, and Morris William Travers, the action of acetylene on the acetates of mercury, T., 127’0 ; P., 1902,183. Burrows, Harry. See ?Tillia.m August- u s Tilden. c. Cain, John Canzell, and Frank Nicoll, the rate of decomposition of diazo- compounds. Part I. Diazo-compounds of the benzene series, T., 1412 ; P., 1902, 186. - .- rate of decomposition of diazo- compounds. Part 11. Diazo-com- pounds of the naphthalene series, P., 1902, 244. Carpenter, Henry Cort Harold, the oxidation of snhhurous acid to di- thionic a d by getallic oxides, T., 1 ; P., 1901, 212. Carter, Willianz. See Xobert HOWSO?L Pickard. Caven, Robert Martin, the molecular con- figiiration of yliosphoryl chloride and its derivatives, T., 1362 ; P., 1901,26.Chapman, David Lconnrd, and Frank Austin Lidbury, the decomposition of water vapour by the electric spark, T., 1301 ; P., 1902, 183. Chattaway, Frederick Daniel, nitrogen chlorides containing the propionyl group, T., 637 ; P., 1902, 64. - nitrogen bromides containing the propionyl group,T., 814 ; P.,1902,113. - substituted nitrogen chlorides con- taining the azo-group, T., 982 ; P., 1902, 174. - a new type of substituted nitrogen chlorides, P., 1902, 165. -__ transformation of diacetanilide into acetyl-p-aminoacetophenone, I)., 1902, 173. - the transformation of diazoamino- into aminoazo-comDounds. and of hydrazobenzene in& benAdine, P. 1902, 175. Chat taway, Frethick Daytiel, and Kenitedy Joseph Previte Orton, the transformation of acetylchloroamino- benzenes into the isomeric chloro- acetanilides, P., 1902, 200.Chattaway, Trederick Daniel, and John Hello Wadmore, the constitution of hydrocyanic, cyanic, and cyanuric acids, T., 191 ; P., 1902,5 ; discussion, P., 6. -- nitrogen chlorides and bromides derived from ortho-sub- stituted snilides, T., 984 ; P., 1902, 173. -- the Cloez reaction, P., 1902, 56 ; discussion, P., 57. Clayton, Edwy Godwirt, on an incrusta- tion from the Stone Gallery of St. Paul’s Cathedral, P., 1901, 201. - asbestos, P., 1901, 203. - phosphorus sesquisulphide and its behaviour with Mitscherlich’s test, P., 1902, 129. Clowes, Fyank, the chemical change produced by the immersion of lead in distilled water, P., 1902, 46.Cohen, J~clius Berend, and Sanmel Henry Clifmd Briggs, menthyl formyl- plienylacetate, P., 1902, 172. Cohen, Julius Berend, and H k r y Drys- dale Dakin, note on the reduction of trinitrobertzene and trinitrotoluene with hydrogen sulphide, T., 26 : P., 1901, 214. -__ the chlorination of the di- chlorotoluenes in presence of the alumininm-mercury couple. The con- stitution of the trichlorotoluenes, T., 1321 ; P., 1902, 183. __- the constitution of the nitro- and dinitro- derivatives of the di- chlorotolucnes, T., 1344 ; p., 1902, 184. _- _- the constitution of the pro- ducts of nitration of In-acetotolnidide, P., 1902, 240. Cohen, J d i m Bercnd, and J. T. Thomp- son, the action of sodium hypochlorite on benzenesulphonanilide, P., 1901, 262. Collie, John Norntan.See Thomas Tickle. Crocker, James Codrington, the picrimino- thiocarbonic esters, T., 436 ; P., 1902, 51. Crofts, James Murray. See Robert Selby Morrell. Crompton, Wollnnd, specific heat of gases, P., 1902, 188 ; discussion, 1’. , 189. - the specific heat of liquids, P., 1902, 235.INDEX OF AUTHORS. 1621 Crossley, Arthzw William, preparation and properties of 4-isopropyldihydro- resorcin, T., 675 ; P., 1901, 172 ; 1902, 86. Crossley, Arthur William, and Henry RondeE Le Sueur, substituted dihy- drobenzenes. Part I. A24-Dinietl~yl- clihydrobenzene, T., 821 ; P., 1901, 245. - 3:5-dichloro-o-xylene and 3:5- dichloro-o-phthalic acid, T., 1533 ; P., 1901, 190. - action of phosphorus haloids on dihydroresorcins. Part I. Diniethyl- dihydroresorcin, P., 1902, 238.D. Dakin, Hmyy Drysdale. See Julius Berend Cohen. Davis, Wil liam Avred, 2 :4 -dibromo- 5 - nitro- and 2:4-dibromo-3:5-dinitro- toluenes, and their behaviour on reduction, T., 870 ; P., 1902, 118. Dawson, Harry itfedforth, the molecular complexity of acetic acid in chloroform solution, T., 521 ; P., 1902, 60. - the solvent properties of mixed liquids in relation t o the chemical characters and solvent properties of their components, T., 1086 ; P., 1902, 179. Dawson, Harry ilh?dforth, and x. Gawler, the existence of polyiodides in nitro- benzene solution, I., T., 524 ; P., 1902, 69. Daweon, Harry &fedforth, and F. E. Grant, a method of determining the ratio of distribution of a base between two acids, T., 512 ; P., 1902, 68. Denison, R. B. See Bertram D. Steele.Divers, Edward, and Masafnka Ogawa, preparation of sulphamide from am- monium amidosulphite, T., 504 ; p., 1902, 71. Dixon, Augustus Edward, the action of phosphorus thiocyanate on alcohol, T., 168 ; P., 1901, 260. -- the action of metallic thiocyanates on carbonyl chloride, P., 1902, 240. Dobbie, James Johnstone, and Alexander Lander, corydaline. Part VII. The constitution of corydaline, T., 145 ; P., 1901, 252. -- the relationships of cory- daline to berberine ; berberidic acid, T., 157 ; P., 1901, 255. Dobbie, Janm Johnstone. See also Walter AToel Eartley. Donnan, Frederick George, and Henry Basaett, jun., [and, in part, Chrlcs James John Fox], the colour changes exhibited by the chlorides of cobalt and some other metals, from the stand- point of the theory of electroaffinity, T., 939 ; P., 1902, 164.Donnan, FTeilerick George. See also Edward Charles Cyril Baly. Dowzard, Edwin, the estimation of strychnine and brucine in nux vomica, P., 1902, 220. Dyson, Gibson, and Arthur Harden, the combination of carbon monoxide with chlorine under the influence of light, P., 1902, 191 ; discussion, P., 191. E. Easterfield, YILOHLC~S HzlZ. See TVilZinm Eyre, John Vnrgm. See Baphnel Mel- Hobson Mills, dola. F. Farmer, Bobcrt Ci-osbie. See Percy Faraday Frankland. Fenton, Henry John Horstman, a reagent for the identification of carbamide and of certain other nitrogen coni- pounds, P., 1902, 243 ; discussion, P., 244. Fenton, Henry John Horstiimn, and John Henry Byffel, mesoxalic semi-alde- hyde, T., 426 ; P., 1902, 54. Findlay, Alexayler, the solubility of mannitol, picric acid, and anthracene, T., 1217 ; P., 1902, 172.Forster, Martin Onslow, studies in the camphane series. Part VlI. Con- version of hydroxycamphene into &halogen derivatives of camphor, T., 264 ; P., 1902, 25. - studies in the camphane series. Part IX. Comparison of bromonitro- camphane with bromonitrocamphor, T., 865 ; P., 1902, 116. - B-bromocamphor, P., 1901, 245. - benzylidenecamphoroxime, P., 1902, 90. - the constitution of enolic benzoyl- camphor, P., 1902, 237. - on the isomeric benzoyl derivatives from isonitrosocamphor, P., 1902,238. Forster, Martin Onslow, and E. A. Jenkinson, aa-benzoylnitrocaniphor and aa-benzoyli~clocamphor, P., 19E2, 117. 5 ~ 21622 INDEX OF AUTHORS. Forster, Martin O?tsIow, and (illiss) Frances M.G. Micklethwait, studies in the camphane series. Part VI. S tereoisomeric halogen derivatives of a-benzoylcamphor, T., 160 ; I?., 1901, 267. -- studies in the cariipliatie series. Part IV. vz-Nitrobenzoylcamphor, T., 406 ; P., 1902, 55. Fortey, (JIiss) Emily C. See Sydney Young. Fox, Charles Jcvmes Joha. Sec Rrcdcrick. &orye Donnan. Francis, Fruitcis Ern&, isomeric a(Ldi- tive compoiinds of' dibenzyl ketone aiid cleoxybenzoiii with benzylidcne-p- toluidine, ~)~-~iitrobc~lzylideiicniiiliiie, and benzylicicnc-1iL-nitroaniline, 1'. , 441 ; P., 1902, 53 ; discussion, P., 53. Francis, Francis Ermst, and Xrncst Boroman Ludlam, isonieric additive products of niethyl, ethyl, and propyl benzyl ketones with benzylideneanil- ine, T., 956 ; P., 1902, 132.Frankland, Sir ErZwnrd, memoriallectnre on (Amstrong), P., 1901, 193. Frankland, Percy Faradny, and nobcrt Crosbie Farmer, liquid nitrogen peroxide as a solvent, P., 1902, 47. Frankland, Percy Paraday, Henry Leorwwcl Heathcote, and CZarcitcc Ja7nes Green, the nitration of diethyl monobenzoyl and mono-11-lolnoyl tar- trates, P., 1902, 251. Frankland, Peiscy Faraday, Hoiry Leonard Heathcote, and (illiss) Hilda Jane Hartle, nitrotartaric acid and some of its ethereal salts, P., 1902,250. Fy Re, 1ViZliam A lemncler. See James Walker. G. Garrett, Frcdcric C'hnrZcs, and John Ar)x- strong Smythe, the bases contained in Scottish shale oil, T., 449 ; P., 1900, 190; 1902, 47. Gawler, R. See Harry Xedforth Dawson. Gilbert, Sir Joseph Benry, obituary notice of, T., 625.Gilbody, Alexander FViZZinm, and William Benry Perkin, j m . , brazilin and h=matoxylin. Part IV. Tlic oxidation of trimcthylbrazilin with chromic acid, T., 1010 ; P., 1899, 27 ; Gilbody, Abexnmh William, an;L Charles Henry Graham Sprankling, influence of the methyl group on ring formation, T., 787 ; P., 1900, 224. Glondinning, Tom AldriclL. See IIwace II: Brown. 1900,105. Goodwin, WiZlinm. See Alfred Senier. Gostling, (ilks) MiZdred, the action of Grant, F. E. See Harry Medforth Green, C'lareiice Jcmes. See Percy Fnra- acids on cellulose, P., 1902, 250. Dawson. day Frankland. H. Hall, A l f w d Daniel, and Fraiwis Jose$h Plymen, the deteririination of available plant food in soils by the use of weak acid solveuts, T., 117 ; P., 1901, 239, 265 ; discussion, P., 240.Hall, AZfred Daniel, and Echvarcl JohiL Russell, a niethocl for deterniining small quantities of carbonates, T., 81 ; P., 1901, 241. Ham, A T c h i e Cecil Osborn. See Arthiw Lapworth. Harcourt, Aicgwtihs Gcorge Vernon. See d ~ u ~ h n Angel. Harden, Arthur, and FV'illinm JO?UL Young, glycogen from yeast, T., 1224 ; l'., 1902, 182. Harden, Arthur. See also QibsojL Dyson. Hartle, (Miss) Hilda Jam. See Percy Paraday Frankland. Hartley, Waltc~ Noel, the absorptioii spectra of metallic nitrates, T., 556 ; P., 1902, 67, 239. -. composition of brittle platinam, P., 1902, 30. Hartle y , Wa I t er i\'oc E, Ja m s Joknsto t ~ e Dobbie, and A lexancler Lauder, the absorption spectra of phloroglocinol and some of its derivatives, T., 929 ; P., 1902, 171. Harvey, Alfred IYiZZiccnz, and A r t h r Lapworth, sulphocampholeriecal.Ir- oxylic acid, P., 1902, 142.Harvey, Alfred lvilliffim. See also Arthzu Lapworth. Heathcote, He9~s.y Leo7inrcl. See Percy Fcwnrtay Frankland. Henderson, George Gerald, and Dn~id Prentice, the influence of certain acidic oxides on the specific rotations of lactic acid and potassium lactate, T., 658 ; P., 1902, 88. Hewitt, John Thodore, and Saiiizcel James Manso?L Auld, the relationship between the orientation of substituents in, and the constitution of, benzeneazo- a-naphthol, T., 171 ; P., 1901, 264. -- the action of substituting agents on benzcneazo-fi-naphthol, T. , 1202 ; P., 1902, 180. Hewitt, John I'lzeodore, and T. S. Moore, a modification of Zeisel's method for tlic cstimatinn of mcthoxyl groups, T., 318; P., 1902, 8.INDEX OF AUTHORS.1623 Rewitt, John Thcoclorc, and John AT. Tervet, oxonium salts of fluoran and its derivatives, T., 663 ; P., 1902, 86. Hewitt, Johm Theodore, Alfred John Turner, and Sid7tcy Wedlace Bradley, t h e coildensation of dimethylamino- lmualdehyde with &naphthol, T., 1‘207 ; P., 1902, 181. Hewitt, John Tlwodorc, and Alfred TYilEiam George Woodforde, bromo- nitro-derivatives of fluorescein, T., 893; P., 1902, 128. Ho ff, Jacobus Hcnricus van’t, the Raoult memorial lecture, T., 969 ; P., 1902, 81. Horton, Edzcnwl. See Rmr!j Er7ac.ctn-l Armstrong. Hunter, Albert Edtcrcrd. See Frccleric Stanley Kipping. I. Innes, Willium Ross, the influencc of temperature on association in benzene solution, and the value of thc molecular rise of boiling point for benzene at different temperatures, T., 682 ; I?., 1902, 26 ; discussion P., 28.J. JeEera, Ernest IIagnes. See Leoizcrrci Temple Thorne. Jenkinson, E. A . See M a r t i n Onsloza Fors ter. Jones, Hwmpl~~ey Owcn, the displace- ment of benzyl by methyl in sub- stituted nitrogen compounds, P., 1901, 205. Jones, Humphrey Owen, and Ouwz lVilluns Richardson, the decom- position of oxalacetic acid phenyl- hydrazone in aqneous and acitl solutions, and a new method of deter- mining the conccritration of hydrogcn ions, T., 1140 ; P., 1902, 140. -- the dissociation constants of oxalacetic acid and its phenylhydr- azone, T,, 1158 ; P., 1902, 141. Jowett, IXoo3,cr AZ6ci.t Dic’l&son, ant1 Charlcs E l t y Potter, the vonstitucnts of conimercial chrysarobin, T., 1576 ; P., 1902, 191.X. Kipping, Frederic Stanley, rcsolution of trimethylhydrindoniurn hydroxide into its optically active components, T., 275 ; P., 1902, 33. Ripping, Frederic Stan Icy, resolution of rnethylbeiizylacetic acid into its optical isomerides, P., 1902, 33. - d-methylhydrindone ; the forma- tion of oximes, hydrazones, and semi- carhazones, P., 1902, 34. - isomeric partially racemic salts containing quinquevalent nitrogen. Part VIII. Resolution of the hydrind- amine bromocainphorsulphonates, P. , 1902, 209. - isomeric compounds of the type NR1R2H3, P., 1902, 211. Kipping, Fredcric Stnnlvy, and Albert Edward Hunter, the rcsolutioii of pheno-a-aminocycloheptane into its optical isomerides. Tartrates of pheno- a-aminocyclohcptane slid of hydriud- amine, T., 574; P., 1902, 60.L. Lander, George Dmce, synthesis of imino-ethers. AT- Arylbenzimino- ethers, T., 591 ; I?., 1902, 72. Lapworth, Arthwr, and Archie Cecil Osborn Hann, dcrivativcs of ?L- and iso-butyrylpyruvic acids, T., 1485 ; P., 1902, 141. -- - optically active esters of 0- ketonic and &aldehydic acids. Part I. Bfenthyl formylphenglncetatc, T. , 1491 ; P., 1902, 144. -- - optically active esters of 8- ketonic a i d B-aldehydic acids. Part 11. Menthyl acetoacetate, T., 1499 ; P., 1902, 145. -- the mutarotation of camphor- quinonehydrazoiie and mechanism of simple desmotropic change, T., 1505 ; P., 1902, 143, 146. Lapworth, ATtImr, and AZfred IViZZiaui Harvey, derivatives of- a-aminocani- phoroximc, T., 549 ; P., 1902, 70. Lapworth, Arthur, and 1VaZtcr Bcnr!~ Lenton, the constitution of the acids obtained from a-dibromocamphor, T., 17 ; P., 1901, 148.-__. optically active methylbcnxyl- acetic acid, P., 1902, 35. Lauder, Alexander. 8ec Jccmcs JoJL~L- stoize Dobbie, and Walter A-od Hartley. Leather, Jolm Walter, the sampling of soils, T., 883 ; P., 1902, 125; dis- cussion, P., 125. - some excessively saline Indian well waters, T., 887 ; P., 1902, 127 ; discussion, P., 128. Lees, Frcderie .Herbert, methyl B-methyl- hkxyl kcton(,, T., 1594 ; P., 1902, 193.1624 INDEX OF AUTHORS. Lees, Frederic Herbert, interaction of ketones and aldehydes with acid chlorides ; the formation of benzoxy- olefines and 1 -benzoxycamphene, P., 1902, 213. Lees, Frederic Herbert. Sce also Fredcrick Belding Power. Lenton, ?Vfilter Henry.See Arlhicr Lapworth. Le Sueur, IIenry 12ondel. See Arthur William Crossley. Lewis, Edward Watkin, tribromoplienol bromide (dibroniobenzene ke t odibrom - ide), T., 1001 ; P., 1902, 177. Lidbury, Frank Austin. See David Leonard Chapman. Lowry, Thomas Ji'artin. See Eenry Edward Armstrong. Ludlam, Ernest Botcnzaa, the preparation of mixed ketones by heating the mixed calcium salts of organic acids, T., 1185 ; P., 1902, 132. _- a simple form of Landsberger's apparatus for determining the boiling point of solutions, T., 1193 ; P., 1902, 180. Ludlam, Ernest Bowman. See also Francis Ernest Francis. Lumsden, John S., solubilities of the calcium salts of the acetic series, T., 350 ; P., 1902, 31. - the equilibrium between a solid and its saturated solution a t various teiu- yeratures, T., 363; P., 1902, 31.M. McCrae, John, di-see. -octyl tartrate and di-sec.-octyl dibenzogltartratt, T., 1221 ; P., 1902, 182. McKenzie, Alexander, the resolution of /3-hydroxybutyric acids into its optically active components, T., 1402 ; P., 1901, 213 ; 1902, 185. Madan, Henry Gcorgc, obituary notice of, T., 628. Mallet, Frederic Richard, isometric anhydrous sulphates of the form M"SO,, R,SO,, T., 1546 ; P., 1902, 198. Marsh, James Ernest, the s tereochernical formuh of benzene, T., :961 ; P., 1902, 164. -- the constitution of metallic cyanides, P., 1902, 248 ; discussion, P., 248. Marsh, James Ernest, and 22. de J. Pleming Struthera, auto-reduction of mercury and silver cyanides, P., 1902, 249. Marshall, Charles Robertshaw, and John Harrison Wigner, constitution of certain organic nitrates, P., 1902, 32.Martin, Gcofrey, is argon an elementary substance 1 P., 1901, 259. Meldola, Raphael, and John Yargas Eyre, elimination of a nitro-group on diazo tisation. Dini tro-p-anisidine and derivatives, T., 988 ; P., 1902, 160. Mellor, Joseph Willinnz, the union of liydrogen and chlorine. V. The action 01 light on chlorine gas, T., 1280 ; P., 1902, 169. - the union of hydrogen and chlorine. VI. The period of induction, T., 1292; P., 1902, 170. Mellor, Joseph William, and W. R. Anderson, the union of hydrogen and chlorine. Part IV. The Draper effect, T., 414 ; P., 1902, 32. Mellor, Joseph William, and Edward Jalm Russell, the preparation of pure chlorine and its behaviour towards hydrogen, T., 1272; P., 1902, 166.Menzies, Alan W. Cranbrook, the sensi- tiveness of a thermoregulator, P., 1902, 10. Micklethwait, (Miss) Frances M. G. See Martin Onslow Forster. Miller, Norman Barry John, the amounts of nitrogen, as ammonia and as nitric acid, and of chlorine in the rain-water collected a t Rothamsted. Report to the Lawes Trust committee, I?., 1902, 88. - the ainounts of nitrogen, as nitrates, and chlorine in the drainage through uncropped and unmanured land. Report t o the Lawes Trust Committee, P., 1902, 89. Mills, Wi7liam Hobson, and Thomas Hill Eaaterfield, derivatives of dibenzoyl- mesitylcne, T., 1311 ; P., 1902, 167. Moir, tJrmes, cyanohydroxypyridine de- rivatives from diacetonitrile ; new derivatives of $-lntidostyril, T., 100 ; I?., 1901, 69. __ di-indigotin, P., 1902, 194.Moody, Herbert B. See Xanuce2 Auck- misty Tucker. Moore, 2'. S. See John Theodore Hewitt. Morgan, Gilbert TJ1onzas, influence of substitution on the formation of diazo- nniines and amitioazo-compounds, T., 86 ; P., 1901, 236 ; discussion, I?., 238. - influence of substitution on the reactivity of the aromatic m-diamines, T., 650 ; P., 1902, 87. Morgan, Gilbert Thonzas, [and, in part, with George Marshall Norman], in- fluence of substitution on the formation of diazoaniines and aminoazo-coni- pounds, T., 1376 ; P., 1902, 185.INDEX OF AUTHORS. 1625 Morrell, Robert Selby, and Jams Uurray Crofts, action nf hydrogen peroxide on carbohydrates in the presence of ferrous wlpliatc, 111.) T., 666 ; P., 1902, 55. N. Neville, Allen. See TVillinm Jackson Nicoll, Frank.See John CannelZ Cain. Norman, George Jfamhall. See Gilbert Pope. T~OMW Morgan. 0. Ogawa, Nasataka. Sec Edward Divers. Orton, Kennedy JosepJb Previte, the nitration of s-trihalogen anilincs, T., 490 ; P., 1902, 58. - some s-chlorobromoni troanilines and their derivatives, T., 495 ; P., 1902, 59. - the nitration of s-trihalogen ncet- anilides, T., 500; P., 1902, 73. -the preparation of highly substituted nitroaminobenzenes, T. , 806 ; P., 1902, 111. - the action of chlorine and bromine on nitroaminobenzenes. Part I. s- Trisubstituted chloronitroaminobenz- enes, T., 965 ; P., 1902, 174. - interchange of halogen for hydroxyl in chloro- and bromo-naphthalenedi- azoniuni hydroxides, P., 1902, 252. Orton, Kennedy Joseph Previte. See also Frederick Daniel Chattaway.P. Patterson, Thomas S., thc influence of solvents on the rotation of optically active compounds. Part 111. Influence of benzene, toluene, o-xylene, m-xylene, p-xylene and mesitylerie 011 the rota- tion of ethyl tartrate, T., 1097 ; P., 1902, 133. __ the influence of solvents on the rotation of optically active compounds. Part IT. Influence of iisphthaleiie on the rotation of ethyl tartrate, T., 1134 : P., 1902, 133. Pavlizek, Frantiiek. See Bohuslav Branner. Perkin, Arthur George, myricetin. Part 11.) T., 203; P., 1902, 11. - robinin, violaquercetin, myrti- colorin, and osyritrin, T., 473 ; P., 1901, 87 ; 1902, 58. - notes on luteolin and apigenin, T. , 1174 ; P., 1902, 180. - quercetagetin, P., 1902, 75. Perkin, A,*thzw George, on the destruc- tive distillation of ethyl gallate, P., 1902, 254.Perkin, Arthur George, and John Baymoncl Allison, rhamnazin and rhainnetin, T., 469 ; P., 1900, 181. Perkin, Artht~r George, and hhmvel IIenry CZiforcl Briggs, the colouring matters of grccii ebony, T., 210 ; P., 1902, 11. Perkin, Arthur George, and Alec Bowrixg Steven, purpurogallin, P., 1902, 74, 253. Perkin, A r t h w George, and Edward John Wilkinson, colouring matter from the flowers of Del’ihiniism Con- solicln, T., 585 ; P., 1900, 182. Perkin, Ar.thz6r George, and Charles XieharcE Wilson, a reaction of some phenolic colouring matters, II., P., 1902, 215. Perkin, ArtJLwr George, and E. Yoshitake, constituents of Acacia and Gnmbier Catechzu. Part I., T., 1160 ; P., 1902, 139. Perkin, William Henry, the magnetic rotation of some polyhydric alcohols, hexoses, and saccharobioses, T., 177 ; P., 1901, 256.- magnetic rotation of ring com- pounds : camphor, limonene, carvene, pinene, and some of their derivatives, T., 292 ; P., 1902, 28. Perkin, William Hewy, jzm., on brazilic acid and the constitution of brazilin, T., 221 ; P., 1899, 27 ; 1900, 106 ; 1901, 257. - aa-dimethylglutaconic acid and the synthesis of isocamphoronic acid, T., 246 ; P., 1900, 214. __ brazilin and hzematoxylin. Part IV. On dimethoxycarboxybenzoyl- formic acid, brazilinic acid, &c., T., 1008 ; P., 1902, 147. - brazilin and hwmatoxylin. Part VI. The oxidation of tetramethylhwma- toxylin with chromic acid, T., 1057 ; P., 1899, 27. - action of nitric acid on methyl dimethylacetoacetate, P., 1901, 204.Perkin, William .Henry, jun., and (~Jfiss) A l i c e R Smith, the synthesis of aa-dimethylglutaric acid, of fl-li ydroxy- aa-dirnethylglutaric acid, and of the cis- and tmns-modifications of aa- dimethylglutaconic acid, P., 1902, 214. Perkin, William Henry, lun., and J. Yates, brazilin and hwmatoxy lin. Part 111. The constitution of hzema- toxylin, T., 235; P., 1899, 27, 75, 211 ; 1900, 107 ; 1901, 257.1626 INDEX OF ATJTHORS. Perkin, Willicm X e w y , jm,. See also Alcxndcr 1Villium Gilbody. Perman, Edgar Philij?, tlie influence of salts and other substances on tlic vapour pressure of aqucoos ammoiiin solutioxi, T., 480; P., 1901, 261. Peters, H a i d d , iodoiiinm coiiiponnds of the type IRR”R”’, and the configura- tion of the iodine atom, T., 1350 ; l’., 1902, 184.Pickard, Robcrt .Hozi:son, Ghnrlcs Allen, lt’illinm A u d l c y Bowdler, and lt’iil- 7inm Carter, hydroxyoxaniides, II., T., 1563 ; P., 1902, 197. Plymen, Francis Joseph. See Alfmcl Bn72icl Hall. Pope, William Juckson, and A17eiz Neville, asymmetric optically nctive selenium compounds and tlie scsa- valcncy of selenium and sulphur. cl- and 7-Phenylmethylsclenetinc salts, T., 1552 ; P., 1902, 198. Potter, Clznrlcs Etty. See Booper Albert Bickinson Jowe tt . Power, Prederick BcZrling, and Fredcric Wcrbcrt Lees, the constitnents of the esseiitial oil of Asarzcnt ccLnacieme, T., 59 ; P., 1901, 210 ; discussion, P., 21 1. ~- the constituents of an essential oil of me, T., 1585 ; P., 1902, 192. Power, Frcdcrick Belding, and Prav,k Ehedden, derivatives of gallic acid, T., Prentice, i7flvid.See Gcoco.1.ge Gerc6l.l Henderson. i 3 ; J?., 1901, 242. R. . Randall, TVilliunz B., obituary notice of, T., 629. Raoult, $‘rawyois Jfarie, memorial lcctiirc on, (VAN’T HOFF), T., 969 ; P., 1902, 81. Ray, PmftcZZa Chawlm, dimercurain- nionium nitrite and its haloid deriv- atives, T., 644 ; P., 1901, 96 ; 1902, 85. Report of the Lawes Trust Committee, on the amounts of nitrogen, as ain- monia and as nitric acid, and of chlorine in the rain-watcr collected a t Rothamsted, P., 1902, 88. Report of the Lawes Trust Committee, on the amounts of nitrogen, as 111- trates, and chlorine in the drainage through uncropped and unmaniired land, P., 1902, 89. Eeynolds, Jamas Emerson., presiden till address, T., 609 ; P., 1902, ii. - the relatiom of the elements, T., 612.Reynolds, Jcvnze~ Zmerson., and Rmil A?phonse Werner, the ‘‘ dynamic iso- meiisni ” of thiourea and ammonium thiocyan,ite, P., 1902, 207. Richardson, O m ) ? , It’illnns. See Htcm- p7my Oiccn Jones. Robertson, P. TV., atomic and niole- cular h a t s of fusion, T., 1233 ; P., 1902, 131. Robertson, lViZZinnz, the action of nitric acid on bromopEienolic compounds, T., 1475 ; P., 1902, 189 ; discussion, P., 190. Rosenheim, Otto, the decomposition of compounds of seleniiini and tellndnni by moulds and its influence on tlic biological test for arspnic, P., 1902, 138. Ruhemann, Siegfried, condensation of phenols with estcrs of unsaturated acids. Part VII., T., 419 ; I?., 1902, 45. -- the action of ethyl chlorofiimilrate on monoalkylmalonic esters, T., 1212 ; P., 1902, 181.Ruhemann, Siegfried, and Henry Emrst Stapleton, tetrazoline. Part II., T., 261 ; P., 1902, 30. Russell, Edward John, and Noman Smith, non-existence of the gaseous snlphide of carbon described by Denitiger, T., 1538 ; P., 1902, 197. Russell, Ek2mrd Jo?Lit. See also Alfr*etl Dimicl Hall, nntl Joscph ll’illinm Mellor. Rutherford, E., :m;l Preclei-ick Soddy, the radioactivity of thorium coni- punds. I. An investigation of tlic radioactive emanation, T., 321 ; l’,, 1902, 2 ; discussion, P., 5 . __ -- thc radioactivity of thorimn compounds. 11. The cause and nature of radioactivity, T., 837 ; P., 1902, 120. __ ~ on the condensation points of the tliorinm and radium emanations, l’., 1902, 219. Ryffel, Jolm I c n r y . See Iienry John Horstmnn Fenton.S. Scott, Alexander, atomic weight of tellur- ium, P., 1902, 112. Senier, Alfred, and WiZ2ium Goodwin, the action of methylene diiodide on aryl- acd naphthyl-amines. Diaryl- methylenediamines, acridines, and naphthacridines, T., 280 ; P., 1902, 12.INDEX OF AUTHORS. 1627 Senier, Alfred, and Thomas Walsh, the polymerisation of cyanic acid : cyanuric acid, and cyamelide, T., 290 ; P., 1902, 13. Shaw, Snvills, obituary notice of, T., 630. Shedden, F r a d . See Frederick Be1diiig Power. Shelton, H. AS'. , the molecular condition of borax in solution, P., 1902, 169. Silberrad, Oswald, polymerisation pro- ducts from diazoacetic acid, T., 598; P., 1902, 44. Simpson, Maxwell, obituary notice of, T., 631. Smith, (Miss) Alice E. See ll'illinm Hmry Perkin, j z c a .Smith, Clarence, studies. in the tetra- hydronaphthalene series. I. The diazoamino-compounds of ccr-tetra- hydro-P-naphthalene, T., 900 ; P., 1902, 137 ; discussion, P., 138. Smith, A'orman. See Edicnrcl John Russell. Smythe, Johiz Arnzstrong. See also Frecleric Charlcs Garrett. Soddy, Frederick, the radioactivity of uranium, T., 860 ; P., 1902, 121. Soddy, Frederick. See also 3. Ruther- ford. Sodeau, William Horace, the ciecom- position of chlorates. Part V. Potass- ium chlorate in presence of osities of manganese, and the theory of' per- clilorate formation, T., 1066 ; I?., 1902, 136 ; discussion, P., 136. Spivey, Williant Thomas A'cttiton, obituary notice of, T., 635. Sprankling, Chccrles Henry GTCL?LCL~, note on the localisation of phosphates in the sugar cane, T. , 1543 ; P., 1902, 196.Sprankling, Charles ITenry GrcdicinL. See also lViZ7iawt Arthur Bone, and Abeander l i l l i a m Gilbody. Stapleton, Henry Ernest. See S'&f~*iccZ Ruhemann. Steele, Bertram D., an accurate method of measuring the coinpressibilities of mpours, T., 1076 ; P., 1902, 166. Steele, Bertram D,, and €2. 3. Denison, the transport number of very dilute solutions, T., 456 ; P., 1902, 29. Steven, A7cc Bozuring. See A ~ t l i ~ &orye Perkin. Stevens, Henrg Pot?, thiocnrbaniide hydrochloride, T., / 9 ; P., 1901, 210. Struthers, R. d e J. Fleminy. See Jc6mes Erizest Marsh. Stub bs , Gcolye. See Th o m ~ s Edward Thorpe. T. Taylor, Eohert Llezuellyn, hypoiodous acid, P., 1902, 72. Tervet, Jolt 71, h7. See John Theodore Hewitt.Thompson, J. T. See J d i i u Bereizcl Cohen. Thorne, Leoimrd Temple, and Ernest B m ~ n c s Jeffers, purification of hydro- chloric acid from arsenic, P. ,1902,118. Thorpe, Jocelyih Field, and 1Yilliain John Young, the y/3-dimethylglutaric acids, . and the separation of cis and trans- forms of substituted glutaric acids, P., 1902, 237. Thorpe, Tho?n,as Edzuarcl, and George Stubbs, taxine, T., 874 ; P., 1902,123 ; discussion, P., 124. Tickle, Thomas, and John Norman Collie, some hydroxypyrone derivatives, T., 1004; P., 1902, 170. Tilden, William Augustus, and Harry Burrows, the coiistitutioii of limettin, T., 508; P., 1901, 216. -- some new derivatives of pinene and other terpenes, P., 1902, 161. Titherley, At%It?ti- WriIsk, the action of sodainide and acyl-substituted sod- amides on orpnic estcrs, T., 1520; P., 1902, 186.Travers, Xorris 1Yillin.m. See Emil Burkard. Tucker, Scmuel A iichmicty, and Herbert R. Moody, the prodnction of hitherto unknown metallic borides, T., 14 ; P., 1901, 129. Turner, Alfred Johii. See John T l ~ c o d ~ t : Hewitt. W. Wade, John, the constitution of the metallic cyanides as deduced from their synthetic interactions ; the con- stitution of hydrogen cyanide, T., 1596 ; I?., 1902, 65. Wadmore, John Mello. See Freclerick Daniel Chattaway. Walker, Jtiius, the state of carbon dioxide in aqueous solntion, P., 1902, 246. - qualitative separation of arsenic, antimony and tin, I'., 1902, 2.26 ; discussion, P., 246. Walker, Jaliies, and lV&?iccm Alcmnder Fyffe, the hydrates and solubility of barium acetate, I?., 1902, 246 ; clis- ctission, P., 247. Walker, J , W., the catalytic racemisa- tion of' amygdalin, P., 1902, 198. Walsh, Thomas. See Alfred Senier. Werner, Einil Alphoncc. See Jams3 Emsl-son Reynolds.1628 . INDEX OF AUTHORS. West, Charles Alfred, phosphorus tetr- oxide, T., 923 ; P., 1902, 138. Wheeler, Bichard V. See William Arthur Bone. Whiteley, (Miss) illartha Annie, the oxime of mesoxamide and some allied compounds. Part 11. Disubstituted derivatives, P., 1902, 212. - the action of barium hydroxide on dimethylvioluric acid, Y., 1902, 220. Wigner, Johlt Harrison. See Ci'mrles Robertshaw Marshall. Wilkinson, Edward John. See Arthw GeoTge Perkin. Wilson, Charles Itichnrd. See Arthur George Perkin. Wooaforae, Alfred William George. See Jokn Theodore Hewitt, Y. Yates, J. See William Henry Perkin, p n . Yoshitake, E. See Arthur George Perkin. Young, Sydney, the preparation of absolute alcohol from strong spirit, T., 707 ; P., 1902, 104. Young, Sydney, the vapour pressures and boiling points of mixed liquids. Parts I. and III.,T.,768 ; P., 1902, 107,218. __ correction of the boiling points of liquids from observed to normal pres- siire, T., 777 ; P., 1902, 108. - on mixtures of constant boiling point, P., 1902, 215. Young, Sydney, and (Miss) Emily C. Fortey, the properties of mixtures of thc lower alcohols with water, T., 717 ; P., 1902, 105. __ the properties of mixtures of tho lower alcohols with benzene and with benzene and water, T., 739 ; I?., 1902, 105. -- fractional distillation as a method of quantitative analysis, T. , 752 ; P., 1902, 106. ___- vapour pressures and specific volumes of isopropyl isobutyrate, T., 783 ; P., 1902,108; discussion, P., 109. ~~ the vapour pressures and boiling points of mixed liquids. Part I / . , P., 1902, 216. Young, WiZilliam Joli?~ See A d m r Harden, and Jocelyn Field Thorpe.

ISSN:0368-1645    

DOI:10.1039/CT9028101619

出版商:RSC    

年代:1902

数据来源: RSC

摘要:

INDEX OF STJBJECTS. T RAN SAC T I 0 N 8. 19 0 2. (Marked T,); and also t o Proceedings of the Session 1901-1902, Nos. 241 to 258, Nov., 1901--Dec., 1902 (marked P.). A. Acacia C'ateclzz~, constituents of ( PERKIK and YOSHITAKE), T., 1160 ; P., 1902, 139. Acetanilide, s-trihalogen derivatives, nitration of (ORTON), T., 500 ; P., 1902, 73. 2 :3 :4 :6-tetrabromo-, 2 :3:4-tribromo-6- nitro-, and s-chlorobromonitro-dc- rivatives (ORTON), T., 497 ; P., 1902, 59. isonieric chloro-derivatives, from acetylchloroaminobenzenes (CfwrrA- WAY and OXTON), P., 1902, 200. 2:4- and 4:2-chlorobromo- (CHATTA- WAY and WADMORE), T., 987 ; P., 1902, 173. Acetic acid, dissociation and niolecular complexity of, in chloroform solution (D~wsor;), T., 521 ; P., 1902, 69. Acetic acid, barium salt, solubility and hydrates of (WALKER and PYFFE), P., 1902, 246.cupric salt, action of heat on (ANGEL and HARCOU~~T), T., 1385 ; P., 1902, 185. mercury salts, action of, on acetyleiic (BUERARD and TILAVEIS), T., 1270 ; P., 1902, 183. Acetic acid, ethyl ester, action of sod- amide and its scyl derivatives on (TITHERLEY), T., 1527 ; P., 1902, 187. Acetic acid, cyano-, ethyl ester, action of ethyl bromotrimethylsuccinate on the sodium derivative of (BONE and SPRANKLING), T., 52 ; P., 1901, 243. Acetoacetic acid, nienthyl ester, and its copper, benzoyl, p-nitrophenylhydr- azidc, and semicarbazide derivatives (LAPWORrH and HAXN), T., 1501 ; P., 1902, 145. Acetone, action of sodainide on (TITHER- LET), T., 1526; P., 1902, 186. Aceto-ni-tolnidide, constitution of the products of nitration of (COHEN and DAKIN), P., 1902, 240.Acetyl-p-aminoacetophenone from di- acetanilide (CHAmAwAky), p., 1902, 173. 4-Acetylaminophenol, 2 :3 :6-tr ibromo- and 6-bromo-2-nitro- (ROBERTSON), T., 1478 ; P., 1902, 190. Acetyl-o-bromophenyl nitrogen chloride (CI~ATTAWAY and WADMORE), T., 987; P., 1902, 174. p -Acetylchloroaminoazobenzene (CHATTAWAY), T., 982 ; P., 1902, 174. Acetylchloroaminobenzenes, transforma- tion of, into the isomeric chloro- acetanilides ( CHATTAWAY and 0 RTOX), P., 1902, 200. Acetylchloroamino-26-dibromo-4-nitro-, and -2:46- and -2:64-chlorobromo- nitro-benzenes (ORTON), T., 497 ; P., 1902, 59. tro- and -4-chloro-2:6-dibromo-3-nitro- benzenes (ORroK), T., 503 ; P., 1902, 74. Acetyl-o-chlorophenyl nitrogen bromide (CIIATTAW4Y and WADMORE), T., 987; P., 1902, 174.Acetylene, action of, on the acetates of mercury (BURKARD and TRAVERS), T., 1270 ; P., 1902, 183. Acetylisopropylbutyric acid. See 8-Keto- B-isopro pylhesoic acid. Acid, C10H1803, from the reduction of camphonic acid (LAPWORTH and LENTON), T., 22. C12H1405N2, from the action of potass- ium hydroxide on C,3H,60,hT (PERKIS), P., 1901, 204. Acetylchloroamino-2:46-tribromo-3-ni-1630 INDEX O F SUBJECTS. Acid, CpHlG0,N2! methyl ester, from t h e action of nitric acid on methyl dimethylacetoacetate (PERKIN), P., 1901, 204. C,,H,,O,N, from the oxidation of corydic acid by permanganate (DOBBIE and LAUDEK), T., 156. C19H1605N2, from benzidinedicarboxy lic acid (MoIR), P., 1902, 196. Acid chlorides, interaction of, with aldehydes and ketones (LEES), P., 1902, 213.Acids from the oil of Asarum canaderne (POWER and LEES), T., 72; P., 1901, 210. from oil of rue (POWER and LEES), T., 1589 ; P., 1902, 193. Acids of the acetic series, solubilities of the calcium salts of the (LUMSDEN), T., 350 ; P., 1902, 31. Address, congratulatory, to M. Mar- celliii Berthelot, P., 1901, 250. to the Owens College, Manchester, P., 1902, 64. presidential (REYXOL~S), T., 609 ; P., 1902, 77. Affinities of acids, method of determining (DAWSOX and GRANT), T., 513 ; P., 1902, 68. Alcohols, lower, properties of mixtiires of, with benzene, aud with benzene and water (YOUNG and FORTEY), T., 739; P., 1902,105. properties of mixtures of, with mater (YOUNG and FORTEY), T., 717; P., 1902, 105. Aldehydes, interaction of, with acid chlorides (LEES), P., 1902, 213.B-Aldehydic acids, optically active esters of (LAPWORTH and HAXN), T., 1491,1499 ; P., 1902, 144,145. Alkylmalonic acid, esters, action of ethyl chlorofumarate on (RI-HEMANK), T., 1212; P., 1902, 181. Alkyltricarballylic acids, synthesis of (HONE and SPRANICLING), T., 29; P., 1901, 215. Aluminium, mercury couple, use of, as a halogen carrier (COHEh-and DAKIN), T., 1324; P., 1902, 183. Amines, aromatic, action of diazonium salts 011 (MORGAN), T., 86, 1376 ; P., 1901, 236 ; 1902, 185. primary, test for ( FENTOK), P., 1902, 244. Amino-oxime-oxalic acid and its ethyl CARTER), T., 1575. Ammonia, influence of salts and other substances on the vapour pressure of aqiieons solutions of (PERMA4S), T., 480 ; P., 1901, 261. eSter(PICKARD, ALLEN, BOWDLER, and Ammonium mercuric bromide, chloride, and chlorobromide (RAP), T., 648 ; P., 1902, 85.chloride, iriflueiice of, on the vapour lressure of aqueous ammonia soln- tion (PERMAN), T., 485 ; P. , 1901, 261. nickel chromate (BRIGGS), P., 1902, amidosulphite, preparation and de- composition of (DIVERS and OGA- WA), T., 504 ; P., 1902, 71. Ammonium thiocyanate !nd thiocarb- amide, dynamic isomerism of (RFPNOLDS and WERNER), P., 1902, 20,. thiocyanate, action of picryl chloride on, in alcoholic solution (CEOCKER), T., 436 ; P., 1902, 57. Amygdalin, catalytic racemisation of (WALKER), P., 1902, 198. isoAmyl alcohol, properties of mixtures of, with benzene, and with benzene and water (YOUNG and FORTET), T., 749 ; P., 1902, 106. properties of mixtures of, with water (YOUKG and FORTEY), T., 733; P., 1902, 105.y-Amylodextrin from the action of barley diastase on starch (BAKEI;), T., 1179 ; P., 1902, 134. Analysis, quantitative, fractional distilla- tion as 5 method of (YOUNG and FOETEY), T.,*752 ; P., 1902, 106. Anhydramides, formation of ( AltMSTRONG and L o w ~ r ) , T., 1441; P., 1901, 182. Anhydrobrazilic acid and its oxinie (PERKIN), T., 230; P., 1900, 1 0 6 ; 1901,258. Anhydrotetramethylhsematoxylone and its acetyl derivative (PERKIN), T., 1062. Anhydrotrimethylbrazilone and its acetyl derivative (PERKIN), T., 1017 ; (GILBODY and PERKIN), T., 1043. Aniline, s-trihalogeii, nitration of (ORTON), T., 490, 806; P., 1902, 58, 111. 4-chloro-2:6-dibromo-3-nitro- ( ORTON), T., 504 ; P., 1902, 74. s-chlorobromonitro-derivatives of, and their derivatives (Oit~o:~), T., 495 ; P., 1902, 59.3:5-cZinitro- (COHEN and DAKIN), T., 29 ; I?., 1901, 214. 3-Anilinocrotonic acid, menthyl ester (LAPWOWIX a i d HAKN), T., 1506 ; P., 1902, 145. hilinophenylmethylenecamphoranil and its acetyl derivative (FORSTER), P., 1902, 237. 255INDEX OF SUBJECTS. 1631 Anilino-phosphorylchloride and -phosph- amic acid (CAVEN), T., 1366; P., 1901, 27. Anilino-p-toluidino-phosphoryl chloride and -phosphoric acid, and its ethyl ester (CAVEN), T., 1369; P., 1901, 26. 4-Anisidine, 2:6-dibronio-, and its acetyl Aeoacetamide, iiniuo-, and its salts (SIL- Azoacetic acid, imino-, barium salt (SIL- Azo-compounds,amino-,from diazoamino- compounds (CHATTAWAY), P., 1902, 175. influence of substitution on the BERRAD), T., 600; P., 1902, 44.BE~~RAD), T., 603 ; P., 1902, 44. the rotation of lactic acid and its potassium salt (HENDERSON aiid P., 1902, 237. CI7H,,ON, and its picrate and bronio- liquid, variation with temperature of the surface energy and density of (BALY and DONSAX), T., 907 ; P., 1902, 115. Arsenic, influence of selenium and tellurium on the biological test for (ROSENHEIM), P., 1902,188. C29H,,0,N, and its anhydride, from the condensation of dimetbylamino- benzaldehyde and &naphthol (HEWITT, TURNER, and BRADLEY), T., 1208 ; P., 1902, 181. Bases in Scottish shale oil (GARRETT and SYYTHE), T., 449 ; P., 1900,190 ; on (SENIEB ancl GOODWIN), T., 280 ; 1’. , 1902, 12. Asnmm calmdense, constituents of the molecular rise of boiling point of, a t difl’erent temperatures (INNES), T., 683 ; P., 1902, 26.Association in benzene solution, in- fluence of temperature on (INNES), T., 682 ; P., 1902, 26. Atomic weight of the rare earths, error of the “sulphate method” for the determination of (BRAUNER mid PAVL~EEK), T., 1248 ; P., 1901, 63. pressures and boiling points of mix- tures of (YOUNG and FORTEY), T., 771 ; P., 1902, 107. 2:4:6-tribromo-l-nitroamino-, and 2 :4 :6-trichloro- 1 -nitroamino- (OR- TON), T., 491 ; P., 1902, 59. l-chloronitroamino-2:4:6-trichloro-,1632 INDEX OF SUBJECTS. Benzene, 1:3:5-trinitro-, reduction of, with hydrogen sulphide (COHEN and DAKIN), T., 26 ; P., 1901, 214. nitroamino-, action of chlorine and bromine on (ORTON), T., 965 ; P., 1902, 174. 1-nitroamino-di-, &i-, and -tetra- halogen- and 1-nitroamino-di- and -tri-halogennitro-, preparation of (ORTOK), T., 806 ; I’., 1902, 111.Benzene-5-azo-2:4- and -4:6-diamino-m- xylene, and their diacetgl derivatives (MORGAN), T., 94 ; P., 1901, 237. Benzeneazobromo-a-naphthol and its ethyl ether, and acetyl derivative (HEWITT and AULD), T., 174; P., 1901, 264. Benzene-4- and -2-azo-25 and -4:6- di-chloro-m-phenylenediamines, p - nitro- (MORGAN and NORMAS), T., 1383 ; P., 1902, 185. diamine, and Benzene-6-azo-2-chloro- 3:6-tolylenediamine and their di- benzoyl and diacetyl derivatives (MORGAN), T., 96 ; P., 1901, 237. Benzeneazo-a-naphthol, relationship between the orientation of substituents in, and the constitution of; and its isonieric bromo-compounds and their acetyl derivatives (HEWITT and AULD), T., 171 ; P., 1901, 264.Benzeneazo-&naphthol, action of brom- ine and of nitric acid on (HEWITT and AULD), T., 1202 ; P., 1902, 180. 0-, m-, and p-bromo-, and their acyl derivatives (HEWITT and AULD), T., 1206; P., 1902, 180. Benzene-6-azo-2:4- tetramethyldiamino- toluene, p-nitro- (MORGAN), T., 656 ; P., 1902, 87. Benzene-5-azo-2:4-tolylenediamine and its diacetyl derivative (MOKGAN), T., 94 ; P., 1901, 237. p-bromo-, and its acyl derivatives (MORGAN and NORMAN), T., 1384 ; P., 1902, 185. thalene, o- and m-nitro- (MORGAN), T., 1380; P., 1902, 185. p-nitro-, and its ethyl derivative (MORGAN), T., 99 ; P., 1901, 238. Benzenediaeoaminotetrahydro- B-naph- thalene, p-bromo-, and 0- and p-nitro- (SMITH), T., 904 ; P., 1902, 137. Bexwenesulphonanilide, action of sodium hypochlorite on (COHEN and THOMP- SON), P., 1901, 262, Benzhydroxamic acid ( PIGKARD, ALLEN, ROWDLER, and CAXTEE), T.1573. Benzene-3-azo-5-chloro-2:4- tolylene- Benzene-2-diazoamino-1-chloronaph- Benzidine, formation of, from hydrazo- brnzene (CIIATTAWAY), P., 1902, 175. Benzidinedimalonic acid, ethyl ester (MoIE), P., 1902, 195. Benzimino-ethyl ether, action of sod- amide on (TIrrmmm), T., 1529. Benzoic acid, esters, action of sodamide and its acyl derivatives on (TITIIEE- LEY), T., 1527 ; P., 1902, 187. Benzo-l:4-pyrone. See Chromone. p-Beneoyl-amino- and -chloroamino- azobenzene (CHATTAWBY), T., 983 ; P., 1902, 174. 4-Benzoylaminophenol, 2-bromo-6-nitro- (&)BEETSON), T., 1478 ; P., 1902, 190. Benzoy1;bromo-’ and -chloro-camphors, aa-, a a-, and aa’-m-nitro- (FORSTER and MICRLETHWAIT), T., 409 ; P., 1902, 55.Benzoyl-o- bromophenyl nitrogen bromide and chloride (CHATTAWAY and WAD- MORE), T., 986 ; P., 1902, 173. Benzoylcamphor, enolic, constitution of (FORSTER), P., 1902, 237. enolic 0- and m-nitro-, and the acetyl derivative of the ?n-compound (FOI~STER and MICKLETHWAIT), T., 410 ; P,, 1902, 55. a-Benzoylcamphor, stereoisomeric halo- gen derivatives of (FORSTER and MtCKLETHWAIT), T., 160 ; P., 1901, 257. Benzoyl-o-chlorophenyl nitrogen bromide and chloride (CHArrAwAY and WAD- MORE), T., 984 ; P., 1902, 173. Benzoyldiphenylbenzenylamidine ( L m - DEE), T., 594; P., 1902, 73. aa-Benzoyliodocamphor (FORSTER and JENKINSON), P., 1902, 117. aa-Benzoylnitrocamphor and nitro- ( FORSTER and JENKINSON), P., 1902, 117. 1-Benzoyloxycamphene and Benzoyl- oxyolefines, formation of (LEES), P., 1902, 213.Benzoyltartaric acid, ethyl ester, nitra- tion of‘ (FRANKLAND, HEATHCOTE, and GREEN), P., 1902, 251. Ben’zyl, displacement of, by methyl in substituted nitrogen compounds (JONES), P., 1901, 205. Benzyl alcohol, action of phosphorus trithiocyanate on (DIXON), T., 171 ; P., 1901, 261. 8-Benzylaminocrotonic acid, mentliyl ester (LAPWORTH and HANN), T., 1505 ; P., 1902, 145. Benzylcarboxyaconitic acid, ethyl ester (RTTTIEMANN), T., 1214 ; P., 1902, 181.INDEX OF SUBJECTS. 1633 Benaylideneaniline, isomeric additive products of, with benzyl methyl, ethyl, and propyl ketones (FRANCIS and LUDLAM), T., 956 ; P.,* 1902, 132. Benzylideneaniline, m-ni tro-, isomeric additive compounds of, with de- oxybenzoiii and with dibenzyl ketone (FJ~AXCIS), T., 441 ; P., 1902, 57.Benzylidenecamphoroxime and its ben- zoyl derivative, and plienylcarbamate Benzylidenemethyl isopropyl ketone and its oxime and semicarbazone (LAPWORTH and HANN), T., 1489; P., 1902, 141. Benzylidene-m-nitroaniline, isomeric additive compounds of, with deoxy- benzoin and with dibenzyl ketone (FRANCIS), T., 441 ; P., 1902, 57. Benzylidene-p-toluidine, isomeric addi- tive compounds of, with deoxybenz- oin and with dibenzyl ketone (FRANCIS), T., 441 ; P., 1902, 57. Benzylmethylacetic acid, optically active (LAPWORTH and LENTON), P., 1902, 35. resolution of, into its optical iso- merides (KIPPING), P., 1902, 33. Benzyl methyl, ethyl, and propyl ketones, preparation of (LUDLAX), T., 1186 ; P., 1902, 132.isomeric additive products of, with benzylideneaniline (FRANCIS and Berberidic acid, and its oxidation pro- ducts (DOBBIE and LAUDER), T., 157 ; P., 1901, 255. Berberine, relation of, to corydaline, and its oxidation product (DOBBIE and LAUDER), T., 145, 157; P., 1901, 252, 255, Berberonic acid (DOBBIE and LAUDEI:), T., 159 ; P., 1901, 255. Bisazoxyacetic acid, preparation of (SILBERRAD), T., 601 ; P., 1902, 44. Bisdiazoacetamide (SILBEREAD), T., 604 ; P., 1902, 44. Bisdiazoacetic acid, preparation of (SILBERRAD), T., 602 ; P., 1902, 44. Bisnaphtharonyl, and tetmnitro- (RUHEMANN), T., 423; P., 1902, 46. Boiling point of benzene, niolecular rise of, at different temperatures (INNES), T., 683 ; P., 1902, 26. of liquids from observed t o normal pressure, correction of the (YOUNG), T., 777 ; P., 1902, 108.of mixed liquids (YOUNG and FORTEP): P., 1902, 21G ; (YOUNG), I?., 1902, 218. (t(’ORSTElt), I?., 1902, 90. LUDLAM), T., 956 ; P., 1902, 132. Boiling point and vapour pressures of mixed liquids (YOUNG), T., 768; P., 1902, 107. of solutions, simple form of Lands- berger’s apparatus for determining the (LUDLAM), T., 1193 ; P., 1902, 180. Borax. See Sodium biborate. Boric acid, influence of, on the rotation of lactic acid and its potassium salt (FENDERSON and PRENTICE), T., 662 ; 1 ., 1902, 88. Borides, metallic, new (TUCKEE and hIooDY), T., 1 4 ; P., 1901, 129. Borneol, magnetic rotation and refrac- tion of (PERKIN), T., 309; P., 1902, 29. E-Borneo1 from the oil of Asarzcm cam- dense (POWER and LEES), T,, 63 ; P., Brazilic acid and its salts, oxime, and semicarbazone (PERKIN), T., 226 ; P., 1899, 28 ; 1900, 106 ; 1901, 258.Brazilin, coiistitution of ( PERKIK), T., 221, 1008, 1057; (GILBODY and PERKIN), T., 1040; P., 1899, 27, 75, 241 ; 1900, 107; 1901, 257 ; 1902, 147. degradation of (PERKIN), P., 1902, 147. Brazilinic acid and its salts, methyl ester, phenylhydrazone, hydrate and tetrabromo-derivative (PERKIN), T., 1030. Brucine, estimation of, in nux vomica (DOWZARD), P., 1902, 220. Butanetricarboxylic acids. See a- Methyltricarballylic acids. isoButyl alcohol, properties of mixtures of, with benzene, and with benzene and water (YOUNG and FORTEY), T., 748 ; P., 1902, 105. properties of mixtures of, with water (YOUNG and FORTEY), T., 732 ; P., 1902, 105. tert. Butyl alcohol, properties of mixtures of, with benzene, and with benzene and water (YOUKG and FORTEY), T., 746 ; P., 1902, 105.properties of mixtures of, with water (YOUNG and FORTEY), T., 729 ; P., 1902, 105. Butylenetetracarboxylic acid. See Methylcarboxyaconitic acid. isoBntyric acid, isopropyl ester, vapour pressures and specific volumes of (YOUNG and POrrEY), T., 763; P., 1902, 108. Bntyrylpyrnvic acids, n- and iso-, ethyl esters and salts (LAPWOETH and 1901, 210. HANN), T., 1485 ; P., 1902, 141.1634 INDEX OF SUBJECTS. C. Calcium nitrate, spectrum of (HAWLEY), Camphane, 1:l-bromonitro-, action of phenylhydrazine on ( FORSTER), T., 870; P., 1902, 116. comparison of, with bromonitro- camphor (FORSTER), T., 865 ; P., 1902, 116. Camphene, magnetic rotation of (PEEKIN), T., 316; P., 1902, 29.a-Campholenic acid (FORSTEI~), T., 271 ; P., 1902, 26. Camphonic acid, coils titu tion, reduc tioil, and degradation of ( LAIWORTII and LENTON), T., 18; P., 1901, 148. Camphononic acid, constitution of (Lap- WOETH and LENTOK), T., 18 ; p., 1901, 148. Camphor and its derivatives, magnetic rotation and refraction of' (PERKIN), T., 292 ; P., 1902, 28. optical inversion of, and the mechan- ism of hetero- and meso-sulphona- tion, of homo- and hetero-bromin- ation and dehydration of (ARM- STRONG and LOWRY), T., 1469. snlphonation of (AEMSTRONG and LOWRY), T., 1441, 1462, 1469; P., 1901, 183, 217, 244. Camphor, B-bromo- (FORSTER), P., 1901, 245. 8-bromo- and B-chloro-, and their oximes and benzoyl derivativcs (FORSTER), T., 269 ; P., 1902, 26.B-bromo-, aa'fi-h'ibrorno-, and ap-cli- bromo-a'-nitro- (AHMSTRONG and LOWEY), T., 1464; P., 1901, 217, 244. a-dibromo-, constitution of the acids from (LAPWORTH and LEXTOX), T., 1 7 ; P., 1901, 148. aa-bromonitro-, action of alcoholic silver nitrate, and of pheuylhydr- azine on (FORSTER), T., 867 ; I?. , 1902,. 116. comparison of, with bromonitro- camphane (FORSTER), T., 865 ; P., 1902, 116. 8-chloro-a-bromo- (FORSTER), T., 273 ; P., 1902, 26. isonitroso-, isomeric benzoyl derivatives from (FORSTER), I?. ,1902, 238. P- Camphoranic acid (8-hydrozycnnt- phoror~ic acid), constitution of (LAP WORTH and LENTON), T., 21 ; P., 1901, 148. Camphorenic acid, 1 Bromo-, constitution of (LAPWORTH uric1 LENTOS), T., 18 ; T., 569; P., 1902, 68. P., 1901, 118. Camphoric acid, 6-bromo-, and its methyl ester a i d anhydride (ARMSTRONG and 244: Camphoronic acid, bromiiiation of (LAP- WORTII and LENTON), T., 25.isocamphoronic acid ( ARMSTRONG and syiithesis of (PERKIN), T., 246; P., Camphoroxime, a-amino-, and its salts, dibenzoyl and benzylidciie derivatives, and carbairiide (LAPWORTII and RAXVRY), T., 549; P., 1902, 70. Camphoroximephenylcarbamate, phengl- carbamide of ( LAPWORTH and HARVEY), T., 554 ; P., 1902, 71. Camphor quinonephenylhydrazone (FORSTEE), T., 869. mutarotation and desmotropic forrus P., 1902, 143, 146. Camphorsulphonanhydramide and its bromo- and chloro-derivatives (ARM- STRONG and LOWRY), T., 1448; P., 1901, 183. Camphorsulphonic acid (Reychler), constitution of (ARMSTRONG and LOWRY), T., 1469. bromide, chloride, amide, anhydr- amide, anilide, p-bronioanilidc, a i d piperidides (ARMSTRONG and LOWRY), T., 1447; P., 1901, 182.Camphorsulphonic acid, a-homo- and a-chloro-, and their salts, bromides, chlorides, and amides, and anilide and piperidide of the bromo-acid (ARM- STRONG alld LOWEY), T., 1451 ; P., 1901, 182. LOWRY), T., 1467 ; P., 1901, 217, Lowim), T., 1468. 1900, 214. of (LAPWOXTH arid HAXS), T., 1508; Cane sugar, See Sucrose. Carbamide, influence of, on the vaiionr pressure of aqueous ammoiiia solution (PERMAN), T., 484; P., 1901, 261. Carbamide, thio-. See Thiocarbamicle. Carbohydrates, action of hydrogen per- oxide on, in presence of ferrous sul- phate (MOKRELL and CROFTS), T., 666 ; P., 1902, 55. Carbon monoxide (carbonic oxide), vari- ation with temperature of the density and surface energy of, and vapour pressure of (BALY and DONNAN), T., 907 ; P., 1902,115.combination of, with chlorine, under the influence of light (DYSON and HARDEN), P., 1902, 191. dioxide, state of, in aqueous solution (WALKER), P., 1902, 246. sulphide, gaseous, non-existence of (I~USSELL and SJIITII) T., 1538; P., 1902, 2 97. See also Urea.INDEX OF SUBJECTS. 1635 Carbonates, method of estimating small quantities of (HALL and RUSSELL), l'., 81 ; P., 1901, 241. Carbonyl chloride, action of metallic thiocyanates on (Drxos), P., 1902,240. Carbonyl-di-m-nitrophenyl- and -di-o- tolyl-carbamide ( PICKARD, ALLEK, ROWDLER, and CARTER), 'l'., 1569. Car bony ldi- ph enyl- and - o - t ol yldi thio - carbamidera (Dlxos), P., 1902, 241. Carbonyldithiocarbamide, additive pro- ducts of (DIXON), p., 1902, 240.Carbonylthiocarbimido-phenyl- , -phenyl- benzyl-, -a-naphthyl-, and -11- tolyl- thiocarbamides (DIXON), P., 1902,241. Carboxydimethoxg benzoylformic acid and its salts (PERKIN), T., 1022; (GILBODY and PERKIK), T., 1045. Carboxydimethoxybenzylformic acid (PERKIK), T., 1028. Carboxydimethoxymandelic acid, lactone of (PERKIN), T., 1026. 2-Carboxy-5: 6-dimethoxyphenoxyacetic acid and its silver salt (PEKKIN and YATES), T., 241; P., 1900, 108; (PEKKIN), T., 1061. 2-Carboxy-5-methoxyphenoxyacetic acid (GILBODY and PEBKIS), T., 1043; P., 1902, 148. Carboxymethoxyphenoxylactic acid ('2) (PEKKIN), T., 1029 ; P., 1902, 148 ; (GILBODY and PERKIN), T., 1043. Carvene. See d-Limonene. Catechins and their azobenzene, acetyl and benzoyl derivatives from Acacia and Gambier Catechzrs (PERKIN and YOSHITAKE), T., 1160 ; P., 1902, 139.Cellulose, action of acids on (GOSTLING), P., 1902, 250. Chlorates, decomposition of (SODEAU), T., 1066 ; P., 1902, 136. Chlorine, amount of, in the drainage through uncropped and unnianurecl land (MILLER), P., 1902, 89. amount of, in the rain-water collected a t Rothamsted (MILLEH), P., 1902, 88. preparation of pure, and its behaviour towards hydrowen (MELLOB and RUSSELL), T., 3872 ; P., 1902, 166. evolution of, from the decomposition of potassiuni chlorate in presence of manganese oxides (SODEAU), T. , 1066 ; P., 1902, 136. combination of, with carbon monoxide under the influence of light (DYSON and HARDEN), P., 1902, 191. union of, with hydrogen (MELLOR and ANDERSON), T., 414 ; P., 1902, 32 ; (MELLOR and RUSSELL), T., 1272; P., 1902, 166 ; (MELLOIL), 'l'., 1280, 1292 ; P., 1902, 169, 170.LXXXI. Chlorine, union of, with hydrogen, under the influence of light (MELLOR and ANDERSON), T., 414 ; P., 1902, 32. gas, action of light on (MELLOR), T., 1280 ; P., 1902, 169. Chromates, double, new series of (BRIGGS), P., 1902, 254. Chromium boride (TUCKER and MOODY), T., 16 ; P., 1901, 129. Chromone (benzo-l:4-;oyrone) and its homologues, salts of (RUHEMANN), T., 420 ; P., 1902, 45. Chrysarobin and its acctyl compounds from commercial chrysarobin (JOWETT and PO~TER), T., 1578; P., 1902, 192. Chrysophanic acid and its acetyl deriva- tive (JOWETT and POTTER), T., 1583 ; P . , 1902, 192. Cineol from oil of rue (POWEK and LEES), T., 1590; P., 1902, 193.Cloez reaction (CHATTAWAY and W ~ D - MORE), P., 1902, 56. Cobalt chloride, colour changes of (Dos- ?;AN and BASSETT), T., 939 ; P., 1902, 164. hydioside, action of sulphurous acid on (CARPEN'I'ER), T., 11 ; P., 1901, 212. Cobaltous potassium sulphate (MALLET), T., 1551 ; P., 1902, 198. s- Collidine. See 2 : 4 : 6-Trime thylpyrid- me. Colour changes of cobalt, copper, and ferric chlorides ( DONNAN and BASSETT), T., 939 ; P., 1902, 164. Colouring matters from the flowers of Delphinium Coiisolicla (PERKIN and WILKINSON), T., 585 ; P., 1900, 182. of green ebony (PEKKIX a i d BRIGGS), T., 210 ; P., 1802, 11. phenolic, reaction of (PERKIN and WILSON), P., 1902, 215. Compressibility of vapours, accurai e method of measuring the (STEELE), T., 1076 ; P., 1902, 165.Conductivity of nitrobenzene solutions of iodine and potassium iodide (DAW- SON and GAWLER), T., 532 ; P., 1902, 70. Copper chloride, colour changes of (DON- NAN and BASSETT), T., 955 ; P., 1902, 164. sulphate, influence of, on the vapour pressure of aqueous ammonia solution (PERMAN), T., 487 ; P., 1901, 261. Corydaldine (DOBBIE and LAUDER), T., 146 ; P., 1901, 252. Corydaline aud its constitution id oxidation products (DOBBIE and LAUDER), T., 145 ; P., 1901, 252. 5 s1636 - INDEX OF SUBJECTS. Corydaline, relation of, to berberine (DOBBIE and LAUDEE), T., 145, 157 ; P., 1901, 252, 255. Corydilic acid and Corydic acid and their oxidation (DOBBIE and LAUDER), T., 146 ; P., 1901, 252. Conmarilic acid, mono- and di-chloro- (TILDEN and BURROWS), T., 511 ; P., 1901, 217.Crotonic acid, @-amino-, nienthyl ester (LAPWORTH and HAXN), T., 1505 ; P., 1902, 145. Cyamelide (SEMEI~ and WALSH), T., 290 ; P., 1902, 13. Cyanic acid, constitution of (CHATTA- WAY and WADMORE), T., 191 ; P., 1902, 5. polymerisation of (SEXIER and WALYH), T., 290 ; P., 1902, 13. Cyanogen haloids, coiistitution and re- actions O f (CHA'ITAWAY and WaD- MORE), 192 ; Y., 1902, 5. Cyanuric acid (SENIER and WALW), constitution of (CHIITTAWAY and WADMORE), T., 191 ; P., 1902, 6. Cyanuric acid, t~ichloroimino- ( CHKYI'A- WAY and WADMOI:E), T., 200 ; l'., 1982, 6. rr., 290 ; P., 1902, 13. D. Day aud hour of meeting, discussion on, P., 1901, 208, 235, 249, 261 ; 1902, 1. Dehydrocorydaline ( DOBBIE arid LAUD- ER), T., 145 : P., 1901, 262.Dc &h i.it i z m Co?i so I ida, c 01 nu riii g matter ofthe flowers of (PERKIN and WILKIX- SON), T., 585 ; P., 1900, 182. Density of liquid oxygen, nitrogeii, argon, and carbon monoxide, vnria- tion of, with teiiipcrature ( RALY and DONKAN), T., 907 ; P., 1902, 115. of 3:5-dichloro-l:l-.dimethyl-Az:~-d1- hydrobenzene (PERKIN), T., 828. of dichloro-o-xylene ( PEKKIN), T., 1535. of 1 :1 -dimethyl - A2:Whydrobenzene (PERKIN), T., 836. See also Vapour density. Deoxybenzoin, isomeric additive coni- pounds of, with benzylidene-p- toluidine, m-nitrobenzylideneanilirie, and benzylidene-m-nitroaniline (FRAN- CIS), T., 441 ; P., 1902, 57. Deoxytrimethylbrazilone (PRI~KIN), T., 1018; (GILBODY and PEIWIN), T., 1046. Dextrose (d-glucose, grape sugar), magnetic rotation of (PERKIN), T., 188; P., 1901, 256.Diacetanilide, tFansforrnation of, into acety 1-p-aminoacetophenone (CHATTA- Diacetanilide, 2:4:6-tribromo-3-nitro- 2:6:4-~hlorobromonitro-, 2:3:4:6-tetr(c- bromo-, and 2:4-dibroino-6-nitro- (ORTOS), T., 497 ; P., 1902, 59. Diacetonitrile, preparation of, and cyano-+-lutidostyril derivatives from (MoIR), T., 100 ; P., 1901, 69. 4 :6 - Diace tyltribromocoumarin (TILDE s and BURI~OWS), T., 510; P., 1901, 217. m-Diamines, aromatic, influence of sub- stitution on the reactivity of (MoI~- GAN), T., 650 ; P., 1902, 87. tertiary, action of diazoninm salts and of formaldehyde on (MORGAN), T., Diastase, ungei minated barley, action of, on starch (BAKER), T., 1177 ; Y., 1902,134. Diaz oacetamide and isoDiazoace tamide (SILBERKAD), T., 603; P., 1902, 44.+Diazoacetamide, See Azoacetamide, iniino-. Diazo-pacetaminobenzene chloride, rate of cleconiposition of (GAIN and NICOLL), T., 1436 ; P., 1902, 186. Diazoacetic acid, polymerisation pro- ducts from (SILBERRAD), T., 598 ; P., 1902, 44. Diazoamines, influence of substitution on the forniatioii of (MORGAN), T., 86, 1376 ; P., 1901, 236 ; 1902, 185. 2-Diazoamino-l-chloronaphthalene (MORGAN), T., 98, 1381 ; P., 1901, 237 ; 1902, 185. Diazoamino-compounds, transformation of, into aminoazo-compounds (CHATT- AWAY), P., 1902, 175. Diazoaminotetrahy dro- &naphthalene (SMITH), T., 905 ; P., 1902, 187. Diazobenzene chloride, and o-, WL-, and p-nitro-, rates of decomposition of (CAIN and NICOLL), T., 1415; P., 1902, 186. Diaaobenzene-p-sulphonic acid, rate of decomposition of (CAIN and NICOLL), T., 1429 ; P., 1902, 186.Diazo-compounds, rate of decomposition of (CAIN and NICOLL), T., 1412; P., 1902, 186, 244. Diazogallic acid, ethyl ester (POWER and SHEDDEN), T., 77 ; P., 1901,242. Diazonium (bemendimonium) salts, action of, on aromatic amines (MORGAN), T., 86,1376; P., 1901, 236 ; 1902, 185. GAS), T., 656; P., 1902, 87. WAY), P., 1902, 173. (ORTON), T., 503; P., 1902, 73. 656 ; P., 1902, 87. action of, on tert.wL-dianiines (Moa-INDEX OF SUBJECTS. 1637 Diazotisation of 2 : 3-dinitro-p-anisidine (XELDOLA and EYRE), T., 988 ; P., 1902, 160. Diasotoluene chlorides, o-, m-, and p-, rate of decomposition of (CAIN and NICOLL), T., 1422 ; P,, 1902, 186. Dibenzoylmesitylene, preparation of, and its derivatives (MILLS and EASTERFIELD), T., 1315; P., 1902, 167.Dibenzoylmesitylenic acids, s- and as-, and their salts, oxidation, and rates of esterification (MILLS and EASTER- FIELD), T., 1317 ; P., 1902, 167. Dibenzoyl nitrogen chloride (CHaTTA- Dibenzoyltartaric acid, di-sec. octyl ester (McCRAE), T., 1221 ; P., 1902, 182. Dibenzoyltrimesic acid and its saIts (MILLS and EASTERFIELD), T., 1322 ; P., 1902, 168. Dibenzoylnvitic acids, s- and as-, and their salts (MILLS and EASTERFIELD), T., 1321 ; P., 1902, 167. Dibenzyl ketone, isomeric additive coin- pounds of, with benzylidene-p-toluid- ine, nz-nitrobenzylideneaniline, and benz ylidene-m-nitroaniline (FRANCIS), T., 441 ; P., 1902, 53. Dibenzylmesitylene (MILLS and EASTER- FIELD), T., 1323. Dioarbanilinocarbanilinodixylylmethyl- enediamine (SENIER and GOODWIN), T., 285 ; P., 1902, 12.Dicarbanilinodiphenylmethylenedi- amine (SENIER and GOODWIN), T., 283 ; P., 1902, 12. Dichrysarobin and its methyl ether, and their acetyl compounds (JOWETT and POTTER), T., 1580 ; P., 1902, 192. Dihydrobrarilic acid and its lactone (PERKIN), T., 221 ; P., 1901, 258. Dihydrobrarilinic acid and dinitro-, lactones of (PERKIN), T., 1038; P., 1901, 258. Dihydrohaematoxylinic acid, lactone of, and its salts (PERKIN and YATES), T., 244. Dihydroresorcins, action of phosphorus haloids on (CROSSLEY and LE SUEUB), P., 1902, 238. s-N-Dihydrotetrazinedicarboxylamide (SILBERRAD), T., 605 ; P., 1902, 44. Dihydroxydibeneylmesitylene (MILLS and EASTERFIELD), T., 1323. Di-indigotin (MoIR), P., 1902, 194. Dimethoxyanhydroglycogallol (PERKIN and WILSON), P., 1902, 215.Dimethoxybenzoylpropionic acid and its synthesis (PERKIN), T., 233 ; P., 1901, 258. WAY), P., 1902, 165. 46-Dimethoxycoumaric acid, disodium and disilver salts (TILDEN and BUR- ROWS), T., 511 ; P., 1901, 217. 46-Dimethoxycoumarilic acid, bromo-, . and its potassium salt and methyl ester (TILDEN and BURROWS), T., 509 ; P., 1901, 217. 46-Dimethoxy-a-methylcoumarin and its B-bromo- and 8-hydroxy-derivatives (TILDEN and BURROWS), T., 511 ; P., 1901, 217. Dimethylacetoacetic acid, methyl ester, action of nitric acid on (PERKIS), P., 1901, 204. Dimethylaminobenzaldehyde, condensa- tion of, with &naphthol (HEWITT, TURNER, and BRADLEY), T., 1207; P., 1902, 181. Dimethyldibromoethylace tic acid (hexaic acid, dibromo-) (PEXKIN , T., 257.aa-Dimethylbutane-ai38- triaarboxg lic acid (hexanetricarboxylic acid) (BONE and SPRANKLING), T., 52 ; P. 1901, 244. aa-Dimethylbutyrolactone (PERKI~ , T., 257. 1:l-Dimethyl-A2:4-dihydrobenzene aid its oxidation products and dibroniido, hydrobromide, and nitrosochloride (CROSSLEY and LE SUEUR), T., 832 ; P., 1901, 245. physical properties of (PERKIN), T., 836. 1:1-Dimethyl-A2:4-dihydrobenzene, 3:5- dichloro-andi its oxidation (CKOSS- LEY and LE SUEUR), T., 826 ; P., 1901, 245 ; 1902, 238. physical properties of (PERKIN), T., 828. Dimethyldihydroresorcin ( CROSSLEY aiid LE SUEUR), P., 1902, 958. action of phosphorus pentachloride on, and its hydrochloride (CROSSLEY and LE SUEUR), T., 821 ; P., 1901, 245. action of phosphorus haloids on, and its anhydride (CROSSLEY and LE SUEUR), P., 1902, 238.Dimethylfluoran nitrate and sulphates (HEWITT and TERVET), T., 665 ; P., 1902, 86. aa-Dimethylglntaconic acid (pentenedi- carboxylic acid), cis- and trans-, synthesis of (PERKIN and SMITH), P., 1902, 214. and its oxidation and distillation. and ethyl ester (PERKIN), T., 2531 P., 1900, 214. au-Dimethylglutaric acid (pentaisedi= carboxylic acid), synthesis of ( P m K i N and SMI~’H), P., 1902, 214. 5 8 21638 INDEX OF SUBJECTS. aa- Dimethylglutaric acid (pentanecli- eurbosylic acid), bromo-, ethyl ester, and the action of alcoholic potash on (PERKIK), T., 252 ; P., 1900,214. a 3-dibromo- (PERKIK), T. , 254. a@-Dimethylglutaric acid (pentanedi- carboxylic acid), czs- and trans-, separation of, and its imide and a-cyano-derivatives (THORPE and YOUNG), P., 1902, 247.Dimethylmalonic acid (propanediciwb- oxylic acid) (PERKIN), T., 255 ; P., 1900, 214. aS-Dimethylpropanetricarboxylic acid (pcntanelrical.bo3--?Jlic acid) (THORPE and YOUNG), P., 1902, 248. Dimethylpyridines, 2:4-, 2 5 , and 2:6-, from Scottish shale oil (GARRETT and 1902, 47. 2 4- Dime thy lp yridine , 6 -amino - 3 - cyano - (MoIR), T., 112 ; P., 1901, 69. Dimethyltricarballylic acids (pentayte- tricarboxylic acids), aa- and ay-, synthesis and dissociation constants of, and their cyano-derivatives, esters, and anhydro-acids (BONE and SPRANK- LING), T., 29 ; P., 1901, 215. Dimethyltrimethylenedicarboxylic acid (EONE and XP~~ANKLING), T., 51 ; P., 1901, 243. Dimethylvinylacetic acid (hexemic acid) (PERKIN), T., 256.Dimethylvioluric acid, action of barium hydroxide on (WHITELEY), P., 1902, 220. Dipentene hydrochloride, magnetic rota- tion Of (PERKIN), T., 307 ; P., 1902,29. Diphenyliodonium bromocamphorsulph- onate (PETERS), T., 1359; P., 1902, 184. Diphenylmethylenediamine and its platinichloride (SEXIER and GOODTVIN), T., 283 ; P. , 1902, 12. a-y-Diisopropyltricarballylic acids (nonanetricarboxylic acids), synthesis and dissociation constants of, and their cyano-derivatives, esters, aud anhydro-acids (BONE and SPRANK- LING), T., 29 ; P., 1901, 216. Dissociation of acetic acid in chloroform solution (DAWSON). T., 521 ; P., 1902, 69. Dissociation constants of alkyltricarb- allylic acids (BONE and SPRANK- LING), T., 37 ; I?., 1W1, 215. of oxalacetic acid a i d its phenylhydr- azone (JONES and RICHARDSON), T., 1168 ; P., 1902, 141.Distillation, fractional, as a method of uantitative analysis (YOUNG and SBIYTHE), T., 451 ; P., 1900, 190 ; 3 OIWEY), ??,, 752 j P., 1902,106. Distribution coefficient, application of, to determine the relative affinities of acids (DAWSON and GRANT), T., 513 ; P., 1902, 68. Dithionic acid, formation of (CARPEN- TER), T., 1 ; P., 1901, 212. D i p toluoyl nitrogen chloride (CHAT- TAWAY), P., 1902, 166. Di-ptolyliodonium salts (PETERS), T., 1358 ; P., 1902, 184. Di-o-, -m, and -p-tolylmethylenediamines (SENIEIL and GOODWIN), T., 283 ; P., 1902, 12. Dixylylmethylenediamine and its platiui- chloride and nitro-derivatives (SEKIE~: and GOODWIN), T., 284 ; P., 1902,12. Drainage water through uncropped and unmanured land, amounts of nitrogen, as nitrates, and chlorine in the (MILLER), P., 1902, 89.Draper effect (MELLOR and ANDERSON), T., 414 ; P., 1902, 32. E. Earths, rare, error of the '' sulphate method " for the determination of the atomic weights of the (BRAUNER and Ebony, green, colouring matters of (PERKIN and BsrGGs), T., 210; P., 1902, 11. Electric spark, decomposition of water vapour by the (CHAPMAN and LID- BURY), T., 1301 ; P., 1902, 183. Elements, relations of the (REYNOLDS), T., 612. Enzyme action (BROWN), T., 373 ; I]., 1902,41; (BROWN and GLENDINNING), T., 388 ; P., 1902, 43. Equilibrium between a solid and its saturated solution at various tempera- tures (LUMSDEX), T., 363 ; P., 1802, 31. Erythritol, magnetic rotation of (PEE- KIK), T., 187 ; P., 1901, 256.d-Erythronic acid, and its salts (MoE- BELL and CROFTS), T., 668 ; P., 1902, 55. Ethoxyanilinophosphoric mid, barium salt (CAVEN), T., 1371. Ethoxyanilinophosphoryl amide and chloride (CAVEN), T., 1371 ; P., 1901, 26. p-Ethoxyphenylsuccinamic asid and its alk 1 substituted derivatives (GILBODP an~Smmm,m(t), T., 789 ; P., 1900, 224. p-Ethoxyphenylsuccinimide. See Py- rantin. pEthoxysnccinanilic acid. See p - Ethoxyphenylmccinamic acid. PAVLfCEK), T., 1248; P., 1901, 63.INDEX OF SUBJECTS. 1639 Ethoxy-p-toluidinophosphoric acid, barium salt (CAVEN), T., 1372. X thoxy-p- toluidinophoephoryl amide and chloride (CAVEN), T., 1372 ; P., 1902, 26. Ethyl alcohol, pure, preparation of, from strong spirit (YOUNG), T., 707 ; P., 1902, 104. properties of mixtures of, with benzene, and with benzene arid water (YOUSG and FORTEY), T., 741 ; P., 1902,105.properties of mixtures of, with water (YOVNG and FORTEY), T., 719 ; P., 1902, 105. action of phosphorus trithiocyanate on (DIXON), T., 268 ; P., 1901,260. Ethylbiuret (PICKARD, ALLEN, BOWD- LER, and CARTER), T., 1572. Ethylcarboxyaconitic acid (pe?tte?tetetru- carbomjlic mid), ethyl ester (RUHE- MANX), T., 1214; P., 1902, 181. Ethylenedicarboxylic acid. See Fumaric acid. Ethylhydroxyoxamide and its hydroxyl- amine salt and acetyl derivative (PICICARD, ALLEN, BOWDLER, and CARTER), T., 1572; P., 1902, 197. i-Ethylidenelactic acid. See Lactic acid. Ethylpiperonylcarboxylic anhydride, w-amino- ( DOBBIE and LATJDER), T., 159 ; P., 1901, 256. Eugenol methyl ether from the oil of Asarunz canadense (POWER and LEES), T., 67 ; P., 1901, 210.Excoecarin and its tribenzoyl derivative and dimethyl ether (PERKIX and BRIGGS), T., 212; P., 1902, 11. Excoecarone (PERKIN and BKIGGS), T., 215 ; P., 1902, 11. F. Ferric chloride, colour changes of (Dox- NAS and BASSETT), T., 955 ; P., 1902, 164. hydroxide, action of sulphurous acid on (CARPENTER), T., 8 ; P., 1901, 212. Flavone group, dyeing properties of some members of the (PERKIN and Fluoran nitrate and sulphate (HEWITT and TERVET), T., 6 6 4 ; P., 1902, 86. Fluorescein hydrochloride and sulphates (HEWITT and TERVET), T., 665 ; P., 1902, 86. bromonitro-derivatives, and their diacetyl and dibenzoyl derivatives and sodium salts (HEWITT and WOODFORDE), T., 893 ; P., 1902, 128. WILKINSOX), T., 589. Formaldehyde, action of, on tcrt.-m- diamines (MORGAN), T., 657; P., 1902, 87.Formylphenylacetic acid, inenthyl ester (COHEN and BRIGGS), P., 1902, 172. and its metallic, acetyl, benzoyl, and phenylcnrbaniate derivatives (LAPWORTH and HANX), T., 1491 ; P., 1902, 114. Fractional distillation, See Distillation. Fumaric acid ~ e t h ~ Z c ~ ~ e d i c f f i r B o ~ ~ ~ ~ ~ c acid), chloro-, ethyl ester, action of alkylmaionic esters on (RUIIE- MANS), T., 1212 ; P., 1902,181. action of, on guaiacol, and on a- and &naphthol (RUHENANN), rr., 421 ; P., 1902, -15. 0. Galactose, magnetic rotationof (Psn~rx), T., 189 ; P., 1901, 256. Gallacetophenone methyl ethers (PERRIN and WILSOX), P., 1902, 215. Gallic acid and its acetyl derivatives and their nitro-compounds, and its amino-derivatives, ethyl esters (POWER and SHEDDEN), T., 73 ; P., 1901, 242.Gallic acid, ethyl ester, destructive dis- tillation of (PRRKIX), P., 1902, 254. Gambier Catechn, constituents of (PER- KIN and YOSHITAKE), T., 1160 ; P., 1902, 139. Gases, specific heat of (CROMYTON), P., 1902, 188. Geraniol from the oil of Asnricm cnna- dense (POWER and LEES), T., 66 ; P., d-Glucose. See Dextrose. Glucosone, preparation and oxidation of (MORRELL and CROFTS), T., 666 ; P., 1902, 55. Glutaric acids, substituted, separation of the cis- and trans- forms of (THORPE and YOUNG), P., 1902, 247. Glycogen from yeast and its relation to oyster and rabbit glycogen (HARDEN and YOUNG), T., 1224; P., 1902, 182. Grape sugar. Set: Dextrose. Gnaiacol, action of ethyl chlorofumarate on the sodium derivative of (RUHE- MANN), T., 421 ; P., 1902, 45.Guaiacoloxyfumaric acid and its ethyl ester (RUHEMANN), T., 421 ; P., 1902, 45. 1901, 210.1640 INDEX OF SUBJECTS. R. Raematoxylin, constitution of (PERKIN and YATES), T., 235 ; (PICKKIN), T., 1008, 1057 ; (GILBODY and PERKIN), T., 1040; P., 1899, 27, 75, 241 ; 1900, 107 ; 1901, 257 ; 1902, 147. Haematoxylinic acid and its salts (PERRIN and YATES), T., 243 ; P., 1900, 108. Halogen group, interchange of a, for hydroxyl in bromo- and chloro- naphthalenediazonium hydroxides (ORTON), P., 1902, 252. Heat. See Thermochemistry. Hemipinic acid (DOBBIE and LAUDER), T., 146 ; P., 1902, 252. m-Hemipinic acid(DaBB1E and LAUDBR), . T., 146 ; P., 1901, 252 ; (PERKIN and YATES), T., 242 ; P., 1899, 27, 241 ; 1900, 107, 108 ; (PERKIN), T., 1025, 1062; (GILBODY and PERKIN), T., 1045.Rexahydroxyttnthraquinone. See Ru6- gallic acid. Hexamethylacridine and its additivc salts and bromo- and nitro-derivatives (SENIER and GOODWIN), T., 285 ; P., 1902, 12. Hexamethyletb ylacridinium iodide (SEN- IER and GOODWIN), T., 285 ; P., 1902, 13. Hexanedicarboxylic acid. See P-iso- Propylglutaric acid. Hexanetricarboxylic acid. Sze aa-Di- methylbutane-aB6-tricsrboxylic acid. Rexenoic acid (dimeth~~uiitylcccetic acid) (PERKIN), T., 256. Hexoic acid, dibrorno-. See Dimethyl- dibromoeth ylacetic acid. sec.Hexy1acetoacetic acid, ethyl ester, and its hydrolysis (LEES), T., 1594 ; P., 1902, 193. Hippurylbenzamide (TLTHERLEY), T., 1532 ; P., 1902, 187. Hydrazobenzene, transformation of, into benzidine ( CHATTAWAY), P., 1902, 175.Hydrindamine bromocamphoraulphon- ates, resolution of ( KIPPING), P. , 1902, 209, 211. dl-Hydrindamine tartrates (RIPPING and HUNTER), T., 583 ; P., 1902, 61. Hydrochloric acid (hydrogen chloride), formation of (MELLOR and ANDER- SON), T., 414; P., 1902, 3 2 ; (UELLOR and RUSSELL), T., 1272 ; P., 1902, 166 ; (MELLOR), T., 1250, 1292 ; I?., 1902, 169, 170. formation of, under the influence of light (MELLOR and ANDERSON), T., 414 ; P., 1902, 32. Hydrochloric acid (hgdroyen chloride), purificatiou of, from arsenic (THORXE and JEFFERS), P., 1902, 118. Hydrocyanic acid (hydrogen cyanide), constitution of (CHATTAWAY and WADXORE), T., 191 ; P., 1902, 5 ; (WADE), T.; 1596 ; P., 1902, 65. Hydrogen, preparation of pure ( MELLOR sud RUSSELL), T., 1279 ; P., 1902, 167.behavionr of, with chlorine ( MELLOR and RUSSELL), T., 1279 ; P., 1902, 167. union of, with chlorine (MELLOR and ANDERSON), T., 414 ; P., 1902, 3 2 ; (MELLOR), T., 1280, 1292; P., 1902, 169, 176. under the influence of light (MELLOE and ANDERSON), T., 414; P.: 1902, 32. union of, with oxygen (BAKER), T., Hydrogen chloride. See Hydroshloric cyanide. See Hydrocyanic acid. Hydrogen peroxide, action of, on carbo- hydrates in presence of ferrous sulphate ( MORRELL and CROFTS), T., 666 ; P., 1902, 55. Hydrogan ions, new method of deter- mining the concentration of (JONES and RICHARDSON), T., 1140 ; P., 1902, 140. o-Hydroxybenzoic acid, See Salicylic acid. 3-Hydroxybenzoic acid, 4:6-dibromo- and 2-bromo-4:6-dinitro- (ROBERT- 4-Hydroxybenzoic acid, 3-ntono- and 315- di-brorno-, acetyl derivatives, and ethyl ester of the dibromo-compound (ROBERTSON), T., 1482; P., 1902,190. P-Hydroxybutyric acid, resolution of, into its optically active components (MCKEXZIE), T., 1402; P., 1901, 213; 1902, 185.l-Hydroxycamphene and its conversion into the &halogen derivatives of camphor, and its methyl and ethyl ethers (FORSTER), T., 264; P., 1902, 25. B-Hydroxycamphoronic acid. See 8- Camphoranic acid. Hydroxycomenic acid (TICKLE and COLLIE), T., 1006; P., 1902, 170. Hydroxydihydrotetramethylhaematoxyl- one, nitro-, and its reactions (PRILKIN), T., 1063. Hydroxydihydrotrimeth ylbrazilone, nitro-, and its acatate (PERKIN), T., 1020; P., 1902, 147; (GILBODP and PERKIN), T., 1048, 400 ; P., 1902, 40. acid. SW), rr., 1484; P., 1902, 190.INDEX OF SUBJECTS.1641 a,-Hydroxy-aa-dirnethylglutaric acid, lactone of, and its silver salt ( YERKIN), T., 259. 8-Hydroxy-aa-dimethylglutaric acid, synthesis of (PERI~IN and SNITH), P., 1902, 214. 6-Hydroxy-2:4-dimethylpyridine. Sce +Ln tidostyril. Hydroxydimethylpyrone and its acetate (TICRI~E autl C‘ormi;), T., 1005 ; l’., 1902, 170. Hydroxyethyldimethylacetia acid, lac- tone of. See aa-Dimethylbutyrolact- one. Hydroxyl, interchange of halogen for, in bronio- and chloro-naphthalenedi- azonium hydroxides (ORTOK), P., 1902, 252. Hydroxylamine, iiem colour reactinn of (BALL), P., 1902, 9. 6-Hydroxy-4-methoxybenzoylpropionic acid (PERKIS), T., 231 ; P., 1901, 258. Hydroxyoxamide and its ethyl ester, silver salt, aud acetyl derivative (PICKARD, ALLEN, I>,OWDI,ER, and CARTER), T., 1565 ; P., 1902, 197.a-Hydroxypropionic acid. See Lnctic acid. Hypoiodous acid (TAYLOR), J?. , 1902, 72. I. Imino-ethers, synthesis of (LAKDER), T., 591 ; I-’. , 1902, 72. Incrustation from the Stone Gallery of St. Paul’s Cathedral (CLAYTON), P., 1901, 201. Inversion temperature. See Thcrmo- chemistry. Iodine, solubility of, in nitrobenzene containing potn-;sium iodide (Daw- SON and GAWLER), T., 528 ; P., 1902, 69. atom, confignratioii of the (PETERS), T., 1350 ; P., 1902, 184. J. Jacarandin and its diacetyl and dibenzoyl derivatives (PERKrN and BRIGGR), T., 217 ; P., 1902, 11. K, Kampherol and its salts, and tribromo- and tetra-acetyl derivatives from the flowers of BeZphiniz6m Cowolidn (PERKIN and WILKINSON), T., 585 ; P., 1900, 182.and its tetra-acetate (PERKIN), T., 475 ; I?., 1901, 57. 3-Xeto-1: l-dimethyl-A4-tetrahydrobenz- ene, bromo-derivativfs aucl 5-chloro- (CROSSLEY and LE SUEUR), P., 1902, 238. Ketones, interactinn of, with acid chlor- ides (LEES), P., 1902, 213. mixed, preparation of, by heating the mixed calcium salts of organic acids (LUDTAM), T., 1185; P., 1902, 132. &Ketonic acids, esters, optically active (LAPWOR~H and HANN), T., 1491, 1499 ; P., 1902, 141, 145. 6-Keto-8-isopropyIhexoic acid and its oxime and seniicarbazide (CROSSLEY), T., 676 ; P., 1901, 172 ; 1902, 86. L, Lactic acid and its potassium salt, in- finence of acidic oxides on the specific rotation of (HENDERSON and PREX- TICE), T., 658; P., 1902, 88. Lactone, Cl4H2,,O2, froiti the oil of Asrtrmt un?indcnse (POWER and LEES), T., 71 ; P., 1901, 210.Lactose (milk super), magnetic rotation of (PlEI:KIN), T., 190 ; P., 1901, 256. Laevulose (d-f.l.icctose), magneti ; rotation Lanthanum, atomic weight of (Brtsume and PAVL~CEK), T., 1243 ; P., 1901, 63. Lanthanum sulphate, new hydrate of Lead, action of distille,L water 011 (CLOWES), P., 1902, 46. Lead nitrate, spectrnm of (HARTLEE‘), T., 570 ; P., 1902, 68. Light. See Photochemistry. Limettin, constitution of, arid its mono- and di-chloro-derivatives (TILDEN and EURR~WS), T., 508 ; P., 1901, 216. Limonene from oil of rue (POWER and LEE>), T., 1590 ; P., 1902, 193. d-Limonene (cnrvcne), magnetic rotation of (PERKIN), T., 292 ; P., 1902, 29. 2-Limonene, magnetic rotation of (PER- KIN), T., 292 ; P., 1902, 29.d-Linalool from the oil of Asarum cnnn- dznse (POWER and LEXS), T., 63 ; P., Liquids, specific heat of (CROBIPTON), P., 1902, 236. correction of tho boiling points of, from observed t o normal pressare (YOIJNG), T., 777 ; P., 1902, 108. mixed, of constant boiling poiat, coni- position of (Pouxc), P., 1902, 215. vapour pressures and boiling points of (YOUNG), T., 768 ; P., 1902, 107, 218 ; (YOUNG and FORTET), P., 1902, 216. of (PERKIN), T , 189 ; P., 1901, 256. (BRAUNEP, and l’.IVLfEEK), T., 1262. 1901,210.1642 INDEX OF SUI3,JECTS. Liquids, mixed, solvcnt propertics of, in relation to tho cheriiical cliaracters and solveut properties of their com- ponents (DAWSON), T., 1086; P., 1902, 179. Lithium nitrate, spectrum of (HARTLEY), T., 565 ; P., 1902, 68.Luteolin and its beiizoyl derivativrs (YEILKIN), ‘l’., 1174 ; P., 1902, 180. Lutidines. See ninietliylpyridiiics. +-Lutidostyril and its 3.5-d’ibromo-, 3- cyario- and 3- and 5-nitro-clerivatives, and -5.carboxylic acid and its 3- nitro-derivative (Rlo~rt), T., 100 ; P., 1901, .69. M, Magnesium nitrate, spcctruin of (HART- LEY), T., 568 ; P., 1902, 68. potassium and rubidium sulphates, anhydrous (MALLET), T., 1548 ; P., 1902, 198. Magnetic rotation. See Photochemistry. Malondihydroxamio acid ( PICKARD, ALLEN, BOWDLER, and CARTE^), T., 1572. Maltose from the action of ungerminated barley diastase on starch (BAKER), T., 1177 ; P., 1902, 134. magnetic rotation of (PERKIN), T., 190 ; P., 1901, 256. Manganic hydroxide, action of sul- phurous acid on (CARPEYTER), T., 10 ; Manganous potassium, rubidium and thallous sulphates, arihydrous (MAL- LET), T., 1549 ; P., 1902, 198.Mannitol, magnetic rotation of (PERKIN), T., 188 ; P., 1901, 256. influence of, on the vapour pressure of aqueous ammonia solution ( PEK- MAN), T., 484 ; P., 1901, 261. solubility of, in water (FISDLAP), T., 1217 ; P., 1902, 172. m-Meconine (PERKIN), T., 1027 ; (GIL- Memorial lectures : Frankland (ARM- STRONG), P., 1901,193; Haoult (VAN’T HOFF), T., 969; P., 1902, 81. Menthol, magnetic rotation of ( PERKIN), T., 309 ; P., 1902, 29. Xercury ahuninium couple, use of, as a halogen carrier (COHEN and DAKIK), T., 1324; P., 1902, 183. Dimercurammonium bromide, chlor- ide, and nitrite, and mercuric brorn- ide and chloride (RAY), T., 644 ; P., 1901, 96 ; 1902, 85.Mercuric ammonium bromide, chloride, and chlorobron~icie (I~AY), T., 645 ; P., 1902, 8.5. P., 1901, 212. BOUY and PEKKIN), T., 1042. Mercury acetylidcs ( RUIXARD ant1 cyanide, auto-reduction of (MARSH Mesityl oxide ( w t h y 1 isobzitemj kctone; iso1’,.op?/Zitleizcnceton c) (TIT 11 ERLEY), T., 1526 ; l’., 1902, 187. Mesitylene, iit flneiicc of, on the rotation of ethyl tartrate (1’A’I‘rEILSOS), T., 1097 ; l’., 1902, 133. Mesoxalic semi-aldehyde (FmTcm and Mesoxamide, oxime of, derivatives of Metallic cyanides constitution of (WADE), T., 1596; P. 1902, 6 6 ; nitrates, absorptioit spectra of (HART- LEY), T., 556; P., 1902, 67, 239. thiocyanates, action of, oit carbonyl chloride (DISON), P., 1902, 240. Methane, pparation of, and slow oxidation of, a t low temperatures 1902, 51.Methoxyanilinophosphoric acid, barium Methoxyanilinophosphoryl chloride (CAYEN), T., 1373, Methoxyl groups, modification of Zeiscl’s method for the estimation of ( HEWI~T and hlOoRE), T., 318 ; P., 1902, 8. Methoxyphosphoryl chloride ( CAVEN), T., 1373. p-Methoxysalicylic acid (PERKIS), T., 231, 1021 ; P., 1900, 106 ; 1901, 258 ; 1902, 147 ; (GILBODY and PERRIN), T., 1053; P., 1899, 28; 1900, 106. Methoxy-p-toluidinophosphoric acid, barinm and potassium salts (CAVEN), T., 1374. Methoxyy-toluidinophosphoryl chlor ide Methyl, displacement of beiizyl by, in substituted nitrogen compounds (JONES), P., 1901, 20.5. Methyl alcohol, prop-rties of mixtures of, with benzene, and with benzene and water (YOUNG and FORTEY), T., 740 ; Y., 1902, 105. properties of mixtures of, with water (YOUNG and F o R r ~ r ) , T., 718 ; P., 1902, 105.Methyl isobutenyl ketone. See Mesityl oxide. Methylcarboxyaconitic acid (butylene- tctmcnr.boqZic acid), ethyl ester (RUHE- MANN), T., 1213; P., 1902, 181. Methylene diiodide, action of, on aryl- and natphthyl-amines (SENIER and a o o n w r ~ ) , T., 250; I?., 1902, 12. rrliA\TEliS), l’., 1271; P., 1902, 18.3. and STBUTHERS), P., 1902, 249. ltYPPEIJ), T., 426 ; l’., 1902, 54. (WHITELEY), P., 1902, 212. (h‘fAlXH), P., 1902, 248. (BONE and \\7REET~RR), T., 535 ; P., Salt (CAYEN), ‘1’ , 1374. (CAYEN), T., 1374.INDEX OF SUBJECTS. 1643 Methylenedimethylsuccinic acid (BONE and SPRANKLIKG), T., 51 ; P., 1901, 243. Methylethylphenacylthetine salts (POPE and NEVILLE), T., 1558 ; P., 1902,199.Methyl group, influence of, on ring formation (GILBODY and SPRANR- LIKG), T., 787 ; P., 1900, 224. Yethylheptylcarbinol. See Nonyl alcohol. Methyl heptyl ketone and its carbazone from oil of rue (POWER and LEES), T., 1588 ; P., 1902, 193. d-Metbylhydrindone arid its oximes, hydrazones and semicarbazones ( KIPP- ING), P., 1902, 34. Xethyl 8-methylhexyl ketone and its oxime and semicarbazone (LEES), T., 1595 ; P., 1902, 193. Methylnonylcarbinol. See Undccyl alcoh 01. Methyl nonyl ketone and its semicarb- azone from oil of sue (POWER and LEES), T., 1588 ; Y., 1902, 193. 2-Methylpyridine. See Picoline. Methylpyridinetricarboxylic acid, in. p. 208" (DOBBIE and LAUDER), T., 146 ; P., 1901, 252. a-Methyltricarballylic acids (bzcta?ixtri- carboxylic acids), synthesis and dis- sociation constants of, and their cyano- derivatives, esters, and anhydro-acids (BONE and SPRANKLING), T., 29 ; P., 1901, 215.Milk sugar. See Lactose. Molecular complexity of acetic acid in chloroform solution (DAWSON), T., 521 ; P., 1902, 69. solution volume in relation to the rotation of ethyl tartrate in various solvents (PATTERSON), T., 1131 ; P., 1902, 138. weight. See Weight, molecular. Molybdenum boride (TUCKER and MOODY), T., 16; P., 1901, 129. Myricetin and its te trabroin o-derivatire and pentamethyl ether and its acetyl compound, and hexaethyl ether (PERKIN), T., 203; P., 1902, 11. Myricitrin and its hydrolysis (PERKIN), T., 207 ; P., 1902,ll. Myrticolorin, identity of, with osyritrin and violaquercitrin (PERKIN), T., 477 ; P., 1901, 88 ; 1902, 58.N. Naphthacridines, u- and 8-, and their salts, and the nitro-derivatives of the a-compound (SENIER and GOODWIN), T., 288 ; P., 1902. Naphthalene, formula of (MARSH), T., 963 ; P., 1902, 165. Naphthalene, influence of: on the rota- tion of ethyl tartrate (PATTERSON), T., 1134 ; P., 1902, 133. Naphthalene-2-aeo-B-naphtho1, l-chloro- (MORGAN), T., 1381 ; P., 1092, 185. B-Naphtha1enediazoaminotetrahydro-B- naphthalene (SNITH), T., 906 ; P., 1902, 137. Naphthalenediazoninm hydroxides, bromo- and chloro-, interchange of halogen for hydroxyl in (ORTON), Y. 1902, 252. Naphtharonylacetic acid, ethyl ester, and amide (RUHEMANN), T., 425 ; P., 1902, 46. S-Naphthol, condensation of, with di- methylaminobenzaldehy de (HEW ITT, TURNER, and BRADLEY), T., 1207 ; P., 1902, 181.Naphthols, a- and /3-, action of ethyl chlorofuniarate on the sodiuni de- rivatives of (RUHEMANN), T., 422 ; P., 1902, 45. a-Naphthoxyfnmaric acid, ethyl ester (RUHEMANN), T., 426 ; P., 1902, 45. 8-Naphthoxyfumaric acid and its ethyl ester (RUHEMANN), T., 422 ; P., 1902, 45. p- Naphthylamine, 1 -nitro- , action of nitrous acid on (MORGAN), T., 1381 ; P., 1902, 185. Naphthylamines, action of methylene diiodide on (SENIER and GOODWIN), T., 280; P.,.1902, 12. Nickel ammonium chromate (BRIGGS), potassium sulphate (MALLET), T., Nitrates, organic, constitution of (&~AR- SHALL and WIGNER), P., 1902, 32. Nitric acid, absorption spectra of (HART- LEY), T., 559; P., 1902, 67, 239. Nitrogen, amount of, as ammonia and as nitric acid, in the rain-water collected a t Rothamsted (MILLER), P., 1902, 88.amount of, as nitrates, in the drainage through uncropped and unmanured land (MILLER), P., 1902, 89. liquid, variation with temperature of the surface energy and density of (BALY asd DONNAN), T., 907 ; P., 1902, 115. quinquevalent, isomeric salts contain- ing (KIPPING), P., 1902, 209, 211. Nitrogen bromides containing propionyl (CHATTAWAY), T., 814; P., 1902, 113. bromides and chlorides, derived from ortho-substituted anilides (CHATTA- WAY and WADYORE), T., 984 ; P., 1902, 173. P., 1902, 255. 1550 ; P., 1902, 198. *1644 INDEX OF SUBJECTS. Nitrogen chlorides containing propionyl substituted (ORTON), T. , 497, 503 ; - P., 1902, 59, 73; (CHATTA- containing the azo- group (CHAT- TAWAY), T., 982; P., 1902,174. peroxide (tetroxide), liquid, as a solvent (FE-QNKLAKD and FARMER), P., 1902, 47.Nitrogen compounds, substituted, dis- placement of benzyl by methyl in (JONES), P., 1901, 205. isolitroao-. See Oximino- or under the Parent Substance. Nonanetricarboxylic acids. See ay- Diisopropy ltricarballylic acids. Nonyl alcohol (methyl-n-heptylcarbinol) from oil of rue (POWER and LEES), T. , 1592 ; P., 1902, 193. Norbrazilinic acid (PERKIN), T., 1035. Nux vomica, estimation of brucine and strychnine in (DOWZ-~RD), P., 1902, 230. (CHATTAWAY), T., 637 ; P., 1902, 64. WAY), P., 1902, 166. 0. Obituary notices :- Sir Joseph Henry Gilbert, T., 625. Henry George Madan, T., 628. W. B. Randall, T., 629. Saville Shaw, T., 630. Maxwell Simpson, T., 631. William Thomas Newton Spivey, T., 635. 242’:4’-0ctamethyltetra-aminoditolyl- 5:b’-methane and its picrate (Mon- GAN), T., 657 ; P., 1902, 87.Osyritrin, identity of, with violaquer- citrin and myrticolorin (PERKIN), T,, 477 ; P., 1901, 88 ; 1902, 58. Oxalacetic acid and its phenylhydrazone, dissociation constants of (JONES and RICHARDSON), T., 1158 ; P., 1902, 141. phenylhydrazone and p-bromo-, de- composition of, in aqueous and acid solutions (JONES and RICHARDSON), T., 1140 ; P., 1902, 140. Oxalic acid, ethyl ester, action of soda- mide on (TITHERLEY), T., 1529 ; P., 1902, 187. Oxalodihydroxamic . acid (PICKARD, ALLEN, BOWDLEB, and CARTER), T., 1572. BOWDLER, and CARTER), T., 1566; P., 1902, 197. Oxanilide,. nz-nitro- (PICKARD, ALLEN, ROWDLER, and CARTER), T., 1569. Oxamphenylhydrazide( PIcKARD,ALLEN, Oxanilphenylhydrazide and o-, m- and p-nitro- (PICKARD, ALLEN, BOWDLER, and CARTER), T., 1567 ; P., 1902, 197.Oximinocamphor, isomeric benzoyl de- rivatives from (FORSTER), P., 1902, 238. a-Oximino-ketones, characteristic reac- tion of (WEITELEY), P., 1902, 218. Oximinomalondi-alkyl- and -aryl-amides and their salts (WHITELEY), P., 1902, 312. Oximinomalon-o- tolylamic acid, ethyl ester (WHITELEY), P., 1902, 212. Oxyazo-compounds, constitution of (HEWITT and AULD), T., 171 ; Y., 1901, 264. Oxygen, evolution of, from tho deconi- position of potassium chlorate in presence of the oxides of manganese (SODEAV), T., 1066 ; P., 1902, 136. liquid, variation with temperature of the density and surface energy of (RALY and DONNAN), T., 907 ; P., 1902, 115. union of hydrogen with (BdKER), T., 500 ; P., 1902, 40.P. Palmitic acid from the oil of AsartLitL camdense (POWER and LEES), T., 61 ; P., 1901, 210. Dimethylglutaric acids. Pimelic acid (isopropylszminic acid). Trimethylsuccinic acid. Pentanetricarballyic acids. See :- ab- Dimeth ylpropane tricarboxylic acid. Dimethyltricarballylic acids. Pentenedicarboxylic acid. See aa-Di- methylglutaconic acid. Pentenetetracarboxylic acid. See Ethyl- carboxyaconitic acid. Perchlorate formation, theory of (SODEAU), T., 1066 ; P., 1902, 136. Period of induction in the reaction between chlorine and hydrogen (MEL- LOR), T., 1292; P., 1902, 170. isoPersulphocyanic acid, forniation of (DIXON), T., 168 ; P., 1901, 261. Pheno-a-aminocycloheptane, resolution of, into its optical isomerides; salts of and its benzoyl derivative (KIPPING and HUNTER), T., 574; P., 1902, 60.Phenol, C9H1202, from the oil of Asarum canctdense (POWER and LEES), T., 60 ; P., 1901, 210. Phenol, absorption spectra of (HARTLEY, DOBRIE, and LAUDRR), T., 933 ; P., 1902, 172. Pentanedicarboxylic acids. See :-INDEX OF SUBJECTS. 1645 - I - Phenylallophanic acid, 712- and p-nitro-, ethyl esters (PICKARD, ALLEX, Bow-u- LEK, and CARTER), T., 1669. Phenol bromide, tr ibro tn o- (dibromob~m- e m h-ctodibronzitle) (LEWIS), T., 1001 ; P., 1902, f i 7 . Phenol, trinitro-. See Picric acid. Phenol compounds, bromo-, action of nitric acid on (ROBERTSON), T., 1475 ; P., 1902,. 189. Phenols, conddiisation of, with esters of unsaturated acids (RUHEMANN), T., 419 ; P., 1902, 45. Phenolphthaleinanhydride.See Fluoran. Phenyl methyl selenide (POPE mid NEVILLE), T., 1553 ; P., 1902, 198. Phenylacetic acid, ethyl ester, action of sodium benzamide on (TITHERLEY), 3- Phenylace timino-ethyl ether, hydro- chloride (LANDEIL),T., 597; P., 1902,73. Phenylacetone. See Benzyl methyl ketone. Phenyl acetyl nitrogen chloride, chloro- bromoiiitro- sndbroinonitro-derivatives of (ORTON), T., 497, 503 ; P., 19011, .59. 73. fr., 1531 ; P., 1902, 187. T., 1526 ; P., 1902, 187. Phosgene. See Carbonyl chloride. Phenyloxamic acid, o- and p-nitro-, ethyl esters (PICKARD, ALLES, BOWD- LER. and CARTER), T., 1568. Phenyl propionyl nitrogen bromide slid chloride, brorno-derivatives of (CIIATTAWAT), T., 816 ; P., 1902, 113. chloro-derivatives of (CHATTAWAT), T., 639 ; P., 1902, 64. Phenylsuccinimide and its alkgl substi- tuted derivatives, stability of GIL- BODY and SPRANKLIKG), T., SO2 ; P.: 1900, 225.Phenyltetrazolylthiacarbamide (RUHE- Phenyl-p-tolyliodonium salts (PETERS), T., 1353 ; P., 1902, 184. Phenyltrimethylenedicarboxylic acid and its salts and anhydride (RUHE- MASS), T., 1215 ; P., 1902, 181. Phloroglucinol anfl its trimcthyl ether, absorption spectra of ( HAR‘I‘LEY, DOBBIE, and LXDER), ’l’., 929 ; P., 1902, 171. Phorone aiid isoPhorone (TITH ICRLET), MAKN arid STAPLETON), T., 262. CARTER), T., 1568. Phenylcarboxyaconitic acid, ethyl ester (RCHEMAYK), T., 1214 ; P., 1902, 181. Phenylchloromethylenecamphor (FOES- ut-Phenylenediamine, inethylation of (MORGAX.), T., 655 ; P., 1902, 87. ui-Phenylenediamine, 2:5dichloro-, and its acyl derivatives, and the action of diazonium salts on (MORGAN and NORMAN), T., 1382 ; P., 1902, 185.Phenylglycinehydroxamic acid and its sodium salt and acetyl derivative ( PICKARD, ALLEN, BOWDLER, and Phenylhydroxylamine, 3 :5-dinitro- (COHEN and DAKIN), T., 29 ; P., 1901, 214. Phenylhydroxymethylenecamphor (E‘ORSTER), P., 1902, 237. Phenylhydroxyoxamide and o-, m-, and p-nitro-, and their sslts and acetyl derivatives (PICKALLD, ALLEX, Bown- LER, and CARTER), T., 1567 ; P., 1902, 197. Phenylmethylselenetine salts, d- and b- (POPE and NEVILLE), T., 1553 ; P., 1902, 198. s-Phenylmethylsuccinic acid am1 its salts (RUHEMAXN), T., 1216; P., 1902. TER), P., 1902, 237. CARTER), T., 1574. Sniue), P., 1902. sziboxide ( BROWNIKG), I’,, 1901, 243. Phosphoric oxide, vaponr density of (WEST), T., 928 ; l’., 1902, 138.Phosphorus tetroxide ( ~ ? L Q S ~ J ~ O T O S ~ ~ J L O S - phoric oxide (WEST), T., 923 ; P., 1901, 138. sesquisulphide and its behaviour witlr 11Zitscherlich’s test (CLAYTOX), P. , 1902, 129. trithiocyauate, action of, 011 alcohols (Drxos), T., 16s ; P., 1901, 260. Phosphoryl chloride and its derivatives, molecular configuration of (CAVEN), T., 1362 ; P., 1901, 26. Light, influence of, on the combination of carbon monoxide with chlorine (DYSON and HARDEN), P., 1902, 191. action of, on chlorine gas (MELLOI:), T., 1280 ; P., 1902, 169. action of, 011 the combination of chlorine and hydrogen (MELLO~: and ANDEXSO?;), T., 414; P., 1902, 32. Radiations from radium and thorium, condensation points of ( RUTHERFOBD and SODDY.), P., 1902, 219.PHOTOCHEMISTRY :-1646 INDEX OF SUBJECTS. PROTOCHEMISTRY :- Radioactivity, cause .and nature of (RUTHERFORD and Soi)DY), T., 1 837 ; P., 1902, 120. of thorium compoiinds (RUTHER- ' FORD and Sonny), T., 321, 837 ; of uranium (SODDY), T., 860 ; P., 1902, 121. Rotation of optically active compounds, influence of solvents on the (PATTERSON), T., 1097, 1134 ; P., 1902, 133. of lactic acid and its potassium salt, influence of acidic oxides on the (HENDERSON and PRENTICR), T., 658 ; P., 1902, 88. of ethyl tartrate, influence of benz- ene, toluene, 0-, m-, and p - xylene and of mesitylene on the (PATTERSON), T., 1097 ; P., 1902, 133. influence of napthalene on Magnetic rotation of ring compounds (PERKIN), T., 292 ; P., 1902, 28. of some polyhydric alcohols, hexoses, and saccharobioses ( PERKIN), T., 177 ; P., 1901, 256.of 0-bromocamphor (PERKIN), T., 1465. of 3 : 5-dichloro- 1 : 1 -dimethyl-A2:4- dihydrobenzene ( PERKIN),T.,~~~. of 3 :5-dichloro-o-xylene (PERKIN), T., 1535. of 1 : 1 -dirnethyl-A2:'-dihydrobenzene (PERKIN), T., 836. Mutarotation of camphorquinone- hydrazone, and the influence of catalytic agents on it (LAPWORTH and HANN), T., 1508 : P., 1902,143. Refraction of borneol and camphor and its derivatives (PERKIN), T., 317; P., 1902, 29. of B-bromocamphor (PERKIN), T., 1465. of 3 : 5-dichloro-l : 1 -dimethyl-A2:4-di- hydrobenzene (PERKIN), T., 828. of 3:5-dichloro-o-xvlene (PERKIN). P., 1902, 2, 120. i Polarisation :- (PATTERSON), T., 1134; P., 1902, 133. T., 1535. of dimethvl-A24-dihvdrobenzene (PERKIN), T., 836." Spectra, absorption, of metallic nitrates (HARTLEY), T., 556 ; P., 1902, 67, 239. of phenol, phloroglucinol and some of its derivatives, and pyrogallol (HARTLEY, DOBBIE, and LAUDER), T., 929 ; P., 1902, 171. Phthalic acid, 3:5-dichloro-, and its diethyl ester, silver salt, anhydride, anil and imide (CROSSLEY and LE 2-Picoline (2-inethyZpyridine) from Scottish shale oil (GARRETT and SMYTHE), T., 451; P., 1900, 190; 1903, 47. Picric acid, solubility of, in benzene and in water (FINDLAY), T., 1219; P., 1902, 172. Picriminothiocarbonic esters (CROCKER), T., 436 ; P., 1092, 57. Pimelic acid (isopropyZsucci?iic acid ; pentanedicarboxylic acid) ( CROSSLEY), T., 676 ; P., 1901, 172 ; 1902, 86. Pinene from the oil of Asarum canadense (POWER and LEES), T., 61 ; P., 1901, 210.from oil of rue (POWER and LEES), T., 1590 ; P., 1902, 193. and its derivatives, magnetic rotation of (PERKIN), T., 292; P., 1902, 29. derivatives (TILDEN and BURROWS), P., 1902, 161. Plant food, determination of available, in soils by the qse of weak acid solvents (HALL and PLYMEN), T., 117; P., 1901, 239, 265. Platinum, brittle, composition of (HARTLEY), P., 1902, 30. Polyiodides in nitrobenzene solution (DAWSON and GAWLER), T., 524 ; P., 1902, 69. Potassium chlorate, decomposition of, in presence of the oxides of manganese (SODEAU), T., 1066 ; P., 1902, 136. iodide, solubility of, in nitrobenzene containing iodine (DAWSOY and GAWLER), T., 529; P., 1902, 69. nonaiodide, KI,, probable existence of, in nitrobenzene solution (DAWSON and GAWLER), T., 532; P., 1902, 70.nitrate, spectrum of ( HARTLEY), T., 563 ; P., 1902, 68. sulphate, influence of, on the vapoiir pressure of aqueous ammonia solution (PERMAN), T., 485; P., 1901, 261. cobaltous, magnesium, manganous and nickel sulphates, anhydrous (MALLET), T., 1548 ; P., 1902, 198. Pressure apparatus, constant, for both reduced andincreasedpressures (INNES), T., 684 ; P., 1902, 26. Propanedicarboxylic acid. See Di- rnethylmalonic acid. Propanetricarboxylic acid. See Tri- carballylic acid. Propionanilide, 0- and p-mono-, 2:4- di-, and 2:4:6-tri-bromo- (CHATTA- WAY), T., 817 ; P., 1902, 113. SUEUR), T., 1536 ; P., 1901, 191.INDEX OF SURJECTS. 1647 Propionanilide, chloro-dcrirntires of (CHATTAWAP), T., 639 ; P., 1902, 64. pPropiony1-amino- and -chloramino- azobenzenes (CHATTAWAY), T., 982 ; P., 1902, 174.Propionyl- bromo- and -chloro-amino- benzenes, bromo-derivatives ( C m w A - WAY), T., 816 ; P., 1902, 113. Propionyl-bromo- and -chloro-amino- chlorobenzenes (CHATTAWAY), T., 639 ; P . , 1902, 64. n-Propyl alcohol, properties of mixtures of, with benzene, and with benzene and water (YOUNG and FORTEY), T., 747 ; P., 1902, 105. properties of mixtures of, with water (YOUNG and FORTEP), T., 723 ; l'., 1902, 105. isoPropyl alcohol, properties of mixtures of, with benzene, and with benzene and water (YOUNG and FORTET), T., 744 ; P., 1902, 105. properties of mixtures of. with water - (YOUNG and FORTEY), T., 726 ; P., 1902, 105. 4-isoPropyldihydroresorcin and its silver salt, dioxime, ethyl ether and bromo- derivative (CROSSLEY), T., 678 ; P., 1901, 172 ; 1902, 86.4-isoPropyldihydroresorcylic acid, ethyl ester (CROSSLEY), T., 676 ; P., 1901, 172 ; 1902, 86. 8-isoPropylglutaric acid (Aczmedicas.b- oxylcric m i d ) (CROSSLEY), T., 676 ; P., 1901, 172 ; 1902, 86. isoPropylideneacetone. See Mesityl oxide. iwPropylsuccinanilic acid (CROSSLET), T., 682. isoPropylsuccinic acid ( pcntnizcdicarb- oxylic acid). See Pimelic acid. Purpurogallin and its -carboxylic acid, tetra-acetyl, tribenzoyl, and dibromo- derivatives (PERKIN and STEVEK), P., 1902, 74. trimethyl ether and its acetyi deriva- tive (PERKIK and STEVEN), P., 1902, 253. Purpurogallone and isopurpurogallone 234. Pyrantin (p-ethoxZl~hcn2/lszccc~~~i~ide), and its alkgl snbstituted derivatives, stability of (GrLBoDY and SPRAKK- LING), T., 793 ; P., 1900, 224.Pyridine from Scottishshale oil (GARRETT and SMYTHE), T., 451 ; P., 1900, 190 ; 1902, 47. Pyrogallol, ahsorption spectra of (HAR'I'LEY, DOBBIE, and LAUDER), T., 933 ; P., 1902, 172. (FERKIN and STEVEN), p., 1902, P yruvylphenylhy drazonehydroxamic acid and its salts and acetyl derivative ( PICKAXD, ALLEXT, BOWDLER, and CARTER), 1'. , 1573. Q. Quercetagetin, and its sulpbate, potass- ium salt and ncetyl compound (PEEKIN), P., 1902, 75. Quercetin tetramethyl and tetraethyl ethers, constitution of (PERKIN and A r m s o x ) , T., 471. R. Racemisation, catalytic, of amFgdalin (WALKER), P., 1902, 198. Radiations, and Radioactivity. See Photochemistry. Radium, condensation p i n t of eman- ations from (RUTHERFORD and S o ~ n r ) , P., 1902, 219.Rain-water, nmonnts of nitrogen as ammonia and as nitric acid, and of chlorine in the, collected a t Rotham- sted (MILLEX), P., 1902, 8s. Ratio of distribution of acetic acid between chloroform and water (DAWSOXT), T., 522 ; P., 1902, 69. of a base between two acids, method of determining ( DAWSOK and GRANT), T., 512 ; P., 1902, 68. Refraction. Sect Photochemistry. Residual affinity, part played by, in the formation of substitution derivatives (ARMSTRONG and HORTON), P., 1901, 246. Resins from green ebony (PERKIN slid BRIGGS), T., 219 ; P., 1902, 12. Resorcinol, 4:2-chloronitro-, and its l-methyl ether and dibenzoate (MEL- DOLA and EYKE), T., 999. Rhamnazin and Rhamnetin, constitution of (PERKIX and AI~LISOX), T., 469. Ring compounds, magnetic rotation nf (PERKIN), T., 292 : P., 1902, 28.Ring formation, influence of the methyl gronp on (GILBODY and SPKANKLING), Robinin and its colouring matter (PER- KIN), T., 473 ; P., 1901, S7. Rotation. See Photochemistry. Rubidium magnesium and nianganous sullrhates, anhydrous (MALLET), T., 1549 ; P . , 1902, 198. Rue, oil of, constituents of (POWER and LEES), T., 1585 ; P., 1902, 192. Rufigallic acid ( ~ R K I N ) , P., 1902, 2.54. 'r., 7s: ; P., moo, 224.1648 INDFX 0 1 S. Sacchsrose. Sce Sucrose. Salicyclic acid, 5-?nono- and 3:5-di- bromo-, acetyl derivatives (ROBERT- sox), T., 1481 ; €’., 1902, 190. Salicylbenzamide (‘rITHEHLET), T., 1533 ; P., 1902, 187. Selenium, sexavalency of, and asym- metric optically active compounds of (POPE and NEVILLE), T., 1552 ; I>., 1902, 198.Selenium compounds, decompnsition of, by moulds (ROSRNHEIM), P., 1902, 138. Shale oil, Scottish, bases in (GARRETT and SMYTHE), T., 449 ; P., 1900, 190 ; 1902,47. Silver cyanide,auto-reduction of (MARSH and STRUTHERS), P., 1902, 249. nitrate, spectrum of (HARTLET), T., 560 ; P., 1902, 68, 239. Sodamide and its acyl derivatives, action of, on organic esters and on acetone (TITHERLEY), T., 1520 ; P., 1902,186. Sodium biborate (borar), the molecular condition of, in solution (SHELTON), P., 1902, 169. nitrate, spectrum of ( HARTLEP), T., 567; P., 1902, 68. Soile, sampling of (LEATHER) T., 883 ; P., 1902, 125. determination of available plant food in, by the use of weak acid solvents (HALL and PLYMEN), T., 117 ; P., 1901, 239, 265. Solubility, factors which condition (LUMSDEN), T., 363 ; P., 1902, 31.of potassium iodide in nitrobenzene containi‘ng iodine (DAWSON and GAWER), T., 529 : P., 1902, 69. of the calcium salts of the acetic acid series (LTTMSDEN), T., 350 ; P., 1902, 31. of barium acetate (WATXER and FTFFE), P., 1902, 246. of anthracene, mannitol, and picric acid (FINDLAP), T., 1217 ; P., 1902, 172. of cyamelide and cyanuric acid (SENIER and WALSH), T., 291 ; P., 1902, 13. of iodine in nitrobenzene containing potassium iodide ( DAWSON and GAWLER), T., 528 ; P. 1902, 62. Solutions, very dilute, the transport number of (STEELE and TIEXISON), T., 456 ; P., 1902, 29. Solvent, liquid nitrogen peroxide as a (FRANKLAND and FARMER), P., 1902, 47. Solvent properties of mixed liquids (DAWSON), T., 1086 ; P., l902, 129.SUBJECTS. Solvents,-influence of, on the rotation of optically active compoiinds (PATTER- SON), T., 1097, 1134 ; I?.! 1902, 133. Specific gravity. T See Density. heat. See Thcrmochemistry. rotation. See Photochemistry. volume, See Volume, specific. Spectra. See Yiiotochemis try. Starch, velocity of hydrolysis of, hy diastase (BROWN and GLENDIN- NISG), T., 388 ; P., 1902, 43. action of ungerminated barley difistase on( RAKER), T., 1177 ; P., 1902,134. Strychnine, estimation of, in niix vomica (DOWZAHD) P., 1902, 220. Substance, C,H,N,I and C,H,H,J,, from the action of methyl iodide on tetr- azoline (RUHEMANN and STAPLE- TON), T., 261 ; P., 1902, 30. C,, H,O,, prfpparation of, and use of, for the identification of carbamide and primary amines (FENTON), P., 1902, 244.CIBHl6O5N2, and C,,H,,O,N,, from the reduction of acid (methyl ester) C,4H,S0,N2 (PPRIEIN), P., 1901,204. C,,H,,O,, and its acetyl compound from commercial chrysarohin (JOW- RTT and POTTER), T., 1583 ; P., 1902, 192. C,,H,,O,N,, from the action of nitrous acid on bcnzylidenwamphoroxime (FORSTER), P., 1902, 90. C,,H,,O,, from the action of quinone on escoecarin ( PRRKIN and RRIGGS), T., 215 ; P., 1902, 11. C8,H,,0,, from the action of potassium terricyanide on enolic benzoylcnm- phor (FORSTER), P., 1902, 238. Substitution, influence of, on the re- activity of the aromatic m-diamines (MORGAN), T., 650; P., 1902, 87. influence of, on the formation of diazoamines and aminoazo-com- pounds (MORGAN), T., 86, 1376 ; P., 1901,236 ; 1902, 185. Substitution derivatives, part played hy residual afflnity in the formation of (ARMSTRORQ and ITORTON), P., 1901, 246.Sucrose (saechayosc, cane szbgaT), mag- netic rotation of (PERKIN), T., 189 ; P., 1901, 256. Sugar cane, localisation of phosphates in the (SPRANKIJNG), T., 1543 ; P., 1902, 196. Sulphamide, preparation of, from ammon- ium amidosulphite (DIVERS and OGAWA), T., 504; P., 1902, 71. Sulphatee, isometric anhydrous, of the form M”SO,, R’,SO, (MALLET), T., 1546 ; P., 1902, 198,INDEX OF SUBJECTS. 1649 Sulphocsmpholenecarboxylic acid and its salts (HARVEY and LAPWORTH), P., 1902, 142. Sulphur, soxavalency of -(POPE and NEVILLE), T., 1552; P., 1902, 198. orienting influence of (ARMSTRONG and HORTON), P., 1901, 246. Sulphurous acid, oxidation of, dithionic acid (CARPENTER), T., 1 ; P., 1901, 212.Surface energy of liquid oxygen, nitro- gen, argon, and carbon monoxide, variation of the, with temperature (BALY and DONNAN), T., 907; P., 1902, 115. T. Tartaric acid, ethyl ester, influence of benzene, toluene, o-, m-, and y- xylenes and of mesitylene on the rotation of ( PATTERSON), T., 1097 ; P., 1902, 133. influence of naphthalene on the rotation of (PATTERSON), T., 1134 ; P., 1902, 133. di-sec. -octyl ester (McCRAE), T., 1221 ; Tartaric acid, nitro-, and its esters (FRANKLAND, HEATHCOTE, and HARTLE), P., 1902, 250. Taxine, its mode of extraction, pro- perties, and hydrochloride, sulphate, gold chlorides and methiodide (THORPIT and STUBBS), T., 874 ; P., 1902, 123. Tellurium, atomic weight of (SCOTT), P., 1902, 11.2. Tellurium compounds, decomposition of, by moulds ( ROSENHEIM), P., 1902, 138.Terpenes, derivatives of (TILDEN and BURROWS), P., 1902, 161. Terpenylic acid from isocamphoronic acid (PERKIN), T., 258 ; P., 1900, 215. 2-Terpineol from the oil of Asarzan canadense (POWER and LEES), T., 63 ; P., 1901, 210. Tetra-azo-oo-dimethoxydiphenyl cblor- ide, rate of decomposition of (CAIN and NICOLL), T., 1440 ; P., 1902,186. Tetra-azodiphenyl chlorides, and oo-di- chloro-, rates of decomposition of (CAIN and NICOLL), T., 1438 ; P., 1902, 186. Tetra-azoditolyl chloride, rate of de- composition of (CAIS and NICOTA), T., 1439 ; P., 1902, 186. nr-Tetrahydro-&naphthalene, diazo- amino-compounds of (SMITH), T., 900 ; P., 1902, 137, P., 1902, 182. nr-Tetrahydronaphthsleneazo- B-naph- tho1 (SMITH), T., 90.3 ; P., 1902, 137. Tetrahydro-8 -naphthaleneazo-B-naph- thylamine (SMITH), T., 906 ; P., 1902, 137.Tetramethoxydinitrodibenzyl (GILBODY and PERKIS), T., 1051. 2:4-Tetramethyldiaminotoluene aiid its atlditive compounds (MORGAN), T., 4: 6-Tetramethyldiamino-in - xylene and its additive salts (MOILGAY), T., 654 ; Tetramethylhaematoxylin, oxidation of, x-ith chromic acid (PERKIN), T., 1057 ; P., 1899, 28. oxidation of, with permanganate (PERKIN and YATES), T., 240 ; P., 1899, 27, 75, 211 ; 1900, 107. Tetramethylhaema toxylone (PERK I x), T., 1060 ; P., 1899, 28. Tetrameth yl-m-phenylenediamine (MORGAN), T., 655 ; P., 1902, 87. Tetrazoline and the action of methyl iodide on (RUHEMANN and STarI,K- TOS), T., 261 : P., 1902, 30. Thallium nitrate, spectrum of (HART- LET), T., 561 ; P., 1902, 68. Thallous manganous sulphate, anhydrous (MALLET), T., 1550 ; P., 1902, 198.Inversion temperature of the 'hydrates of barium acetate (WALKER and FTFFE), P., 1902, 247. Thermo-regulator, sensitiveness of R (MENZIES), I?., 1902, 10. Atomic and Molecular heats of fusion (ROBERTSON), T., 1233 ; P., 1902, Specific heat of gases (CROMPTOX), P., Heat of dissociation in benzene sohi- tion (IUXES), .T., 705 ; P., 1902, 27. Heat of reduction of metallic hydr- oxides (CARPENTER), T., 2 ; P., 1901, 212. Heat of solution, relation between and the shape of a sduhility curve (LTTMSDEX), T., 367 ; P., 1902, 32. Thermo-regulator. SeeThermochemistry. Thiocarbamide and ammoninrn, tl I io- cyanate, " dynamic isomerism " of (REYNOLDS and WERNER), P., 1902, 207.hydrochloride (SrrmrExs), T., 73 ; P., 1901, 210. Thorium, condensation point of eniana- tions from (RUTHERFORD and S m m ) , P., 1902, 219. 653 P., 1902, 87. P., 1902, 87. THERMOCHEMISTRT :- 131. 1902, 188. O f liqUidS(CROMPTON), P., 1902,236.1650 INDEX O F SUBJECTS. Thorium compounds, rm?ionetivity of ( RIJTIIERFO~LD and SOD~Y), T., 321, 836 ; P., 1902, 2, 120. Tin, antimony and arsenic, separation of (WALKER), P., 1902, 246. Toluene, influence of, on the rotation of ethyl tartrate (PATTERSOY), T., 1097 ; P., 1902, 133. Toluene, 2 : 4-cli bromo -5 -nitro-, and 2 :4- clibromo-:,:5-minitl.o-, and their reduction (DAYIS), T., 870, P., 1902, 118. six clichloro-derivatives, chlorination of, i n presence of the alnminium- mercury conple (COHEK and DAKIU), T., 1324 ; P., 1902, 183.six trichloro-derivatives, preparation , nitration, and oxidation of (COHEN and DAKIN), T., 1327 ; P., 1902, 183. six ~ichloro-?~zo~zo-and -cli-nitro-deriva- tives, constitution of (COHEN and DAKIN), T., 1344 ; I?., 1902, 184. 2-and 4-chloronitroaniino-3 :5-dibromo- (ORTON), T., 968 ; P., 1902, 175. 2:4:6-trinitro-, rrduction of, with hydrogen siilphide (COHEN and DARIN), T., 26 ; P., 1901, 214. 2- and 4-nitro,zmino-3-5-tlibromo- (ORTON), T., 813 ; P., 1902, 111. p-To1 uene- 5-azo -4:6-d iamino- iri -xylene (MORGAN), T., 95 ; P., 1901, 237. p-Toluene-3-azo-5-chloro-2:4-tolylene- diamine (MOEGAN), T.. 96 ; P., 1901, 297. p-Toluenediazoaminote trahydro-B-naph - thalene (SMITH), T., 90’2; P., 1902, 137. 5-Toluidine, ~ : ~ - d ~ ~ ) r o l i l o - , and its ncetyl derivative (DAVIS), T., 872 ; P., 1902, 111.6-Toluidine, 2:4-(Zinitro- ( COHEX ancl DAKIK), T., 28 ; P., 1901, 214. p-Toluidino-phosphoryl chloride and -phosphamic acid (CAVEX), T., 1367 ; P., 1901, 27. pToluoyltartaric acid, ethyl ester, nitra- tion of ( FRANKLAND, HEATHCOTE, and GREEX), P., 1902, 251. N-o-Tolylacetimino-ethyl ether hydro- chloride (LANDER), T., 597 ; P., 1902, 73. o-Tolylallophanic acid, ethyl ester, and o-Tolylbiuret- ( PICKARD, ALLEN, BOWDLER, and CARTER), T., 1571. N-o- and -p-Tolylbenzimino-e thers ( LAS- DEE:), T., 595; Y., 1902, 73. m-Tolylenediamine, methylation of (MORGA4N), l’., 653 ; P., 1902, 87. s-Tolylenediamine, and its diacetyl derivative (DAVIS), T., 873 ; P., 1902, 11s. Tolylenediamines, 2:4- and 3:5-, 5- and 2-chloro-, and their acyl derivatives (BIORGAN), T., 95 ; P., 1901, 237.6-Tolylhydroxylamine, 2:4-dinitro- (COHEN and DAKIN), T., 27, P., 1901, 214. o-Tolylhydroxyoxamide, and its salts and ncctyl derivativc ( PICKARD, ALLEN, BOWDLER, and CARTER), T., 1571 ; I)., 1902, 197. o-Tolyloxamic acid, ethylester (PICKARD, ALLEN, BOWDLER, and CARTER), T., 1571. Transport numbers of very dilute solu- tions (STEELE and DENISOS), T., 456 ; P., 1902, 29. Triazole nitrate, preparation of (SIL- RERRAD), T., 6 0 2 ; P., 1902, 44. Tricarballylic acid ~~o~cLne-asy-ts.icns.6- oxytic acid), synthesis and dissociation constant of, and its cyano-derivative, esters, and anhydro-acid (Bosii: ancl SPRANKLIXG), T. , 29 ; P., 1901, 215. Trihydroxybutyric acid. See cl-Erythr- onic acid. Trimethylbrazilin, osidation of, with chromic acirl (PERKIN), T., 1016 ; P., 1902, 147 ; ,(GILBODY and PERKIK), T., 1040; P., 1899, 2 7 ; 1900, 105. Trimethylbrazilone ( PERKIS), T., 1017 ; P., 1902, 147 ; (GILBoDY and PERKIS), T., 1040; P., 1899, 2 7 ; 1900, 105. Trimethylhydrindonium hydroxide, re- solution of, into its optically active components (KIPPISG), T., 275 ; P., 1902, 33. 2:46-Trimethylpyridine from Scottish shale oil (GARsE1‘T and SMYTHE), T., 451 ; P., 1900, 190 ; 1902, 47. Trimethylsuccinic acid (pcntmedicarb- oxyZic ucid), brominntion of (BONE and SPKANKLING), T., 50 ; P., 1901, 243. Trimethylsuccinic acid (pentniiedicnrb- oxylic acid), bromo-, ethyl ester, action of, on ethyl sodiocyanoacet ite (BONE and SPKAXELING), T., 5 2 ; P., 1901, 243. Trimethylsuccinic anhydride, bromo- (BONE and SPEASKLING), T., 51 ; P., 1901, 243. Tungsten boricle (TUCKER and MOODY), T., 16 ; P., 1901, 129. U. Undecyl alc3hol (s,tethyZ-n-)LonZiZcnrb- inol) (POWER and LEES), T., 1593; P., 1902, 193. Uranium, radioactivity of (SODDY), T. , 860 ; P,, 1902, 121. Urea, test for (FERTON), P., 1902, 244.INDEX OF SUBJECTS. 1651 V. Vaponr density of phosphorophosphoric and phosphoric oxides (WEST), T., 927 ; P., 1902, 138. See also Density. Vapour pressures and boiling points of mixed liquids (YOUNG), T., 768; P., 1902, 107. of mixed liquids (YOUNG and FOBTEY), P., 1902, 216; (YOUNG), P.; 1902, 218. of aqueous ammonia solution, influ- ence of salts and other substances on the (PERMAN), T., 480; P., 1901, 261. of carbon monoxide (BALY and of isopropy1 isobutyrate (YOUNG and FORTET), T., 783 ; P., 1902, 108. Vapours, compressibility of, accnlate method of measuring the (STEELE), T., 1076 ; P., 1902, 165. Velocity of decomposition of diazo- compounds (CAIN and NICOLL), T., 1412 ; P., 1902,186, 244. Velocity of enzyme action (BROWS), T., 374 ; P., 1902, 41. Velocity of esterification of the two dibenzoylmesityleriic acids (MILLS and EASTERFIELD), T., 1318 ; P., 1902, 168. Velocity of hydrolysis of starch by diastase (BROWN and GLENDINNING), T., 388 ; P., 1902, 43. Velocity of inversion of sucrose (BROWN), T., 376 ; P., 1902, 41. Violaquercitrin, identity of, with osyri- trin and myrticolorin (PEKKIN), T., 477 ; P., 1901, 88 ; 1902, 5s. Volume, specific, of‘ isopropyl isohutyiate (YOUNG and FORTEP), T., 783 ; P., 1902, 108. DOXNAN), ‘r., 919. W. Water, decoinposition of the vapour of, by the electric spark (CHAPMAN and LIDBURY), T., 1301 ; P., 1902, 183. distilled, action of, on lead (CLOWEY), P., 1902, 46. Weight, molecular, cicterii\ination of, by a simple form of Landsberger’s boiling point apparatus ( LUDLAM), T., 1193 ; P., 1902, 180. Well waters, Indian saline (LEATHER), T., 887 ; P., 1902, 127. X. o-Xylene, 3:5-dichloro- (CROSSLEY and LE SUEIJR), P., 1902, 238. preparation of (CROSSLEY and LE SUEUR), T., 1534; P., 1902, 190. densities, magnetic rotation and re- fractive values of ( PERKIN), T., 1535. m-Xylene, 2:4- and 4:6-diamino-, acyl derivatives of (MORGAN), T., 93; P., 1901, 237. Xylenes, o-, w a - aiid p-, influence of, 011 the rotation of ethyl tartrate (PAT- TERSON), T., 1097 ; P., 1902, 133. Xylenol, bromo-derivatives of (CROSSLET and LE SUEUI:), P., 1902, 239. nz-Xylylene-46-diamine, methylation of Y. Yeast, glycogeii from (HAILDEN and 2, Zinc nitrate, spectrum of ( HAXTLEY), T., 569 ; P., 1902, 68. Zirconium boride (TUCKEI: a i d MOOIIY), ‘I!., 15 ; P., 1901, 129. (MORGAN), ‘r., 654; P., 1902, 87. YOUNG), T., 1224 ; P., 1902, 182.

ISSN:0368-1645    

DOI:10.1039/CT9028101629

出版商:RSC    

年代:1902

数据来源: RSC