J O U R N A L OF THE CHEMICAL SOCIETY. TRANSACTIONS. H. F:. ARMsrRosG, Ph.D., F.R.S. J . DEWAR, LL.D., F.R.S. WYNDHAM R. DUNSTAN, M.A., F.R.S. A. VERNON HAILCOURT, M. A., F.R.S. C. T. HEYCOCK, N.A., F.R.S. R. MELDOLA, F.R.S. H. FORSTER MORLEY, M.A., D.Sc. W. RAMSAY, Ph.D., F.R. S. A. SCOTT, M.A., D.Sc., F.R.S. T. E. THORPE, LL.D., F.R.S. W. A. TILDEN, D.Sc.. F.R.S. W. P. WYNNE, D.Sc., F.R.S. @Fb-itar : C. E. GROVES, F.R.S. Sub - &bitor : A. J. GREENAWAY. 1898. Vol. LXXIII. LONDON: GURNEY & JACKSON, 1, PATERNOSTER ROW. 1898.RICHARD CLAY AND EJONS, LIMITED, LONDON AXD n u m A Y .RICHARD CLAY AND EJONS, LIMITED, LONDON AXD n u m A Y .C O N T E N T S . PAPERS READ BEFORE THE CHEMICAL SOCIETY. PAC& 1.-Decomposition of Camphoric Acid by Fusion with Potash or Soda.By ARTHUR WILLIAM CROSSLEY and WILLIAM HENRY PERKIN, jun. . . . . . . . . . 1 11.-Experiments on the Synthesis of Camphoric Acid. Part I. By WILLIAM HENRY BENTLEY and WILLIAM HENRY PERKIN, jun. 45 111.-Synthesis of an Isomeride of Camphoronic Acid. By SAMUEL IV. -Properties and Relationships of Di h ydroxy tartaric Acid. V.-Stereochemistry of Unsaturated Carbon Compounds. Part I. By JOHN J. B. SCHRYVER, Ph.D. . . . . . . . . . 68 Part I. By HENRY J. HORSTMAN FENTON, M.A. . . . 71 Etherificntion of Substituted Acrylic Acids. SUDBOROUGH~~~LORENZOL. LLOYD . . . . . 81 Kekulk Memorial Lecture. By FRANCIS R. JAPP, F.R.S. . . 97 HEIM, Ph.D., and PHILIP SCHIDROWITZ, Ph.D. . . . 139 TI.-Compounds of Piperidine with Phenols. By OTTO ROSEN- Note on the Physiological Action of Guaiacolate of Piper- idine.By F. W. TUNNICLIFFE, M.D., M.R.C.P. . . . 145 VI1.-Action of Chloroform and Alkaline Hydroxides on the VII1.-New Method of Preparing Pure Iodine. By BEVAN 1X.-Action of Alkalis on Amides. By JULIUS B. COHEN, Ph.D., and CHARLES EDWARD BRITTAIN, B.Sc., The Yorkshire College . . . . . . . . . . . . 157 X.-Formation of Monomethylaniline from Dimethylaniline. By JULIUS B. COHEN, Ph.D., and HARRY T. CALVERT, B.Sc., By HENRY J. HORST- Nitrobenzoic Acids. By WALTER J. ELLIOTT, M.A. . . 145 LEAN, B.Sc., B.A., and W. H. WHATMOUGH . . . . 148 The Yorkshire College . . . . . . . . 163 XI.-Volumetric Estimation of Sodium. XI1.-Derivatives of Bromotolylhydrazine, MAN FENTON, M.A. . . . . . . . . . 167 C,H3Br(CH3)(N,H,) [l : 3 : 6.1 By J. T.HEWITT,*M.A., D.Sc., Ph.D., and F. G. POPE . XII1.-Effect of the Mono-, Di-, and Tri-chloracetyl Groups on the Rotatory Power of Methylic and Ethylic Glycerates and Tartrates. By PERCY FRANKLAND, F.R.S., and THOMAS STEWART PATTERSON, Ph.D., late Priestley Scholar in Mason College, Birmingham . . . . . . . . 18 1 . 174 A 2iv CONTENTS. XIV.-Rotation of Ethylic and Methylic Di-monochloracetyltar- By PERCY FRANKLAND, F.R.S., and ANDREW TURN- XV.-A Chemical Investigation of the Constituents of Indian and American Podophyllum (Podophyllum emodi and Podophyllum peltaturn). By WYNDHAM R. DUNSTAN, F.R.S., and THOMAS ANDERSON HENRY, Salters’ Research Fellow in the Laboratories of the Imperial Institute . . XVL-The Volatile Constituents of the Wood of Goupia tomen- tom. By WYNDHAM R.DUNSTAN, F.R.S., and THOMAS ANDERSON HENRY, Salters’ Research Fellow in the Labora- toriesof the Imperial Institute . . . . . . XVI1.-Production of some Nitro- and Amido-oxylutidines. Part I. By Prof. J. N. COLLIE, Ph.D., F.R.S., and THOMAS TICKLE, Salters’ Company’s Research Fellow in the Research Laboratory of the Pharmaceutical Society of Great Britain . XVIII. -Production of some Nitro- and Amido oxylutidines. Part 11. By Miss L. HALL (University College, London), and J. NORMAN COLLTE, Ph.D., F.R.S. (Professor of Chemistry at the Pharmaceutical Society of Great Britain, London) . . By J. NORMAN COLLIE, Ph. D., F.R.S., and COLIN C. FRYE, Pharma- ceutical Society of Great Britain, Bloomsbury Square . . XX.-Benzene Hexabrornide.By FRAXCIS EDWARD MATTHEWS, Ph.D. . . . . . . . . . . . . XX1.-Observations on the Influence of the Silent Discharge on Atmospheric Air. By WILLIAM ASHWELL SHENSTONE and WILTJAM T. EVANS . . . . . . . . . XXI1.-Preparation and Properties of Orthochlorobromobenzene. By JAMES J. DOBBTE, M.A., D.Sc., and FRED. MARSDEN, M.Sc., Ph.D. . . . . . . . . . . XXIII. -Preparation of Dry Hydrogen Cyanide and Carbon Monoxide. By JOHK WADE, B.Sc., and LAURENCE C. PANTING, M.B., B.Ch. . . . . . . . . XX1V.-Manganic Salts. By CHARLES EMMANUEL RICE, B.A. . XXV.-Chemical Properties of Concentrated Solutions of certain Salts. Part I. Double Potassium Carbonates. By WILLIAM COLEBROOK REYNOLDS, ,A.R.C.S. . . . . XXV1.-The Colouring Matters .of the Indian Dye Stuff Asbarg, Delphinium xalil.By ARTHUR GEORGE PERKIN, F.R.S.E., and JULIUS ALDRED PILGRIM . . . . . 11. d n tjhe Oxidation of Fenchene. By JOHN ADDYMAN GARDNER, M.A., and GEORGE BERTRAM COCKBURN, B.A. . . . . . . XXVII1.-Formation of Ethylic Dihydroxydinicotinate from Ethylic Cyanacetate. By Sr ICGFRIED RUREMANN, Yh.D., M.A., and K. C, BROWNING, B.A. . . . . . . trates. BULL, Ph.D. . . . . . . . . . X1X.-Note on the Action of Bromine on Benzene. XXVI1.-Researches on the Terpenes. PAGE 203 209 226 229 235 241 243 246 254 255 258 262 267 275 280CONTENTS. V XX1X.-The Action of Alkpl Iodides on Silver Malate and on Silver Lactate. By THOMAS PURDIE, F.R.S., and G. DRUCE LANDER, B.Sc. . . . . . . . . . . XXX.-The Optical Rotations of Methylic and Ethylic Tartrates. By (the late) JAMES WYLLIE RODGER and J.S. STRAFFORD BRAME . . . . . . . . . . . XXX1.-Position-Isomerism and Optical Activity : the Com- parative Rotatory Powers of Diethylic Mono-benzoyltartrate and Mono-toluyltartrate. By PERCY FRANKLAND, F.R.S., and J. MCCRAE, Ph.D., late Priestley Scholar i n Mason University College, Birmingham . . . . . . XXXI1.-Cis- and trans-Tetramethylene-( 1 : 3)-dicarboxylic Acids and the Condensation of Formaldehyde with Ethylic Malonate. By E. HAWORTH and W. H. PERKIN, JUNR. . XXXII1.-Action of Ferric Chloride on Ethereal Salts of Ketone Acids. By ROBERT SELBY MORRELL, M.A., Ph.D., and JAMES MURRAY CROFTS, B.A., B.Sc. . . . . XXX1V.-Formation of aa’-Dihydroxypyridine. By SIEGFRIED RUHEMANN, Ph.D., M.A. . . . . . . . . XXX V.-The Preparation and Properties of Formaldoxime.By WYNDHAM R. DUNSTAN, M.A., F.R.S., and ARNOLD L. BOSSI, Ph.D. . . . . . . . . . . XXXVL-Action of Ammonia and Substituted Ammonias on Acetylurethane. By GEORGE YOUNG, Ph.D., and ERNEST CLARK . . . . . . . . . . . . . . XXXVI1.-Formation of Oxytriazoles from Semicarbazides. By GEORGE YOUNG, Ph.D., and BENJAMIN MITCHELL STOCKWELL, B.Sc. . . . . . . . . . . . . XXXVII1.-Yellow Colouring Principles contained in various Tannin Matters. Part V. Pistacia lentisczcs, P, teyebin- thus, Tamaris africana, 5”. gaZZica, AiZanthus gkandulosa, Picus curica. By ARTHUR GEORGE PERKTN, F.R.S.E., and PERCIVAL JOHN WOOD . . . . . . . . XXX1X.-Isomeric Bornylainines. By MARTIN ONSLOW FORSTER, Ph.D., B.Sc. . . . . . . . . . . XL.-The Condensation of Chloral Hydrate and Orcinol.By JOHN THEODORE HEWITT, M.A., D.Sc., Ph.D., and FRANK DIXON, B.Sc. . . . . . . . . . . XLL-Sulphonation of Benzophenone and of Diphenylmethane. By ARTHUR LAPWORTH, D.Sc. . . . . . . . XLI1.-Reduction of Bromic Acid and the Law of Mass Action. By WINIFRED JUDSON, B.Sc., and JAMES WALLACE WALKER, M.A., Ph.D. . . . . . . . . . . By H. BRERETON BAKER, M.A. . . . . . . . XLII1.-The Drying of Ammonia and Hydrogen Chloride. PAGE 287 301 307 330 345 350 35 3 361 368 374 386 397 402 410 422vi CONTENTS. PAGE X LIT.-Some Derivatives of Benzophenone. By FRANCIS XLV.-The Chlorine Derivatives of Pyridine. Part I. By WILLIAM JAMES SELL, M.A., F.I.C., and FREDERICK WILLIAM DOOTSON, M.A. . . . . . . . . . . 432 XLV1.-Note on the Action of Chlorine on Pyridine.By WILLIAM JAMES SELL, M.A., F.I.C., and FREDERICK WILLIAM DOOTSON, M.A. . . . . . . . . . . 442 XLVII. -A Possible Basis of Generalisation of Intramolecular Changes in Organic Compounds. By ARTHUR LAPWORTH, D.Sc. 44 5 XLVII1.-The Carbohydrates of Barley Straw. By C. F. CROSS, XL1X.-Reactions of the Carbohydrates with Hydrogen Per- oxide. By C. F. CROSS, E, J. BEVAN, and CLAUDE SMITH . 463 L.-Properties and Relationships of Dihydroxytartaric Acid. Part 11. Salts of the Acids. By HENRY J. HORSTMAN FENTON, M.A. . . . . . . . . . . 472 LI.-AEnity Constants of Dihydroxymaleic, Dihydroxyfumaric, Dihydroxytartaric, andTartronic Acids. By S. SKINNER, M.A. 483 LI1.-Hydrolysis of Starch by Acids. By HAROLD JOHNSON . 490 LII1.-Determination of Molecular Weights.-Modification of By JAMES WALKER LIT.-Rate of Escape of Ammonia from Aqueous Solution.By LV.-Note on the Liquefaction of Hydrogen and Helium. By LV1.-Action of Formaldehyde on Amines of the Naphthalene LVI1.-Action of Hydrogen Bromide in Presence of Ether on Carbohydrates and certain Organic Acids. By HENRY J. HORSTMAN FENTON, M.A., and Miss MILDRED GOSTLING, By SAMUEL BARNETT Stereo- isomeric Derivatives of Camphor. By T. MARTIN LOWRY, B.Sc. . . . . . . . . . . . . 569 By J. NORMAN COLLIE, Ph.D., F.R.S., and W. LEAN, Redwood Research Scholar in the Research Laborahory of the LX1.-Molecular Weights of Permanganates, Perchlorates, and By J. MURRAY CROFTS, B.A., B.Sc., EDWARD MATTHEWS, Ph.D. . . . . . . . 426 E. J. BEVAN, and CLAUDE SMITH . . . . . . 459 Landsberger’s Boiling Point Method.and JOHN S. LUMSDEN . . . . . . . . 502 EDGAR PHILIP PERNAN, D.Sc. . . . . . . . 51 1 JAMES DEWAR, M.A., F.R.S. . . . . . . . 528 Series. Part I. By GILBERT T. NORGIAN, B.Sc. . . . 536 B.Sc., Lond. . . . . . . . . . . 554 SCHRYVER . . . . . . . . . . . 559 LVII1.-Researches on Camphoric Acid. L1X.-Studies of the Terpenes and Allied Compounds. LX.-Production of some Chloropyridinecarboxylic Acids. Pharmaceutical Society of Great Britain . . . . 588 Research Student of Emmanuel College . . . . 593 Periodates in Solution.CONTENTS. vii PAGE LXII. -The Ultraviolet Absorption Spectra of some Closed By W. N. HARTLEY, F.R.S., LXII1.-Enantiomorphism. By FREDERIC STANLEY KIPPING LX1V.-Solubility of Isomeric Substances. By JAMES WALKER LXV.-Constitution of Oleic Acid and its Derivatives.Part I. LXV1.-Reversible Zymohydrolysis. By ARTHUR CROFT LXVI1.-Preparation of a Standard Acid Solution by direct absorption of Hydrogen Chloride. By G. T. MOODY . 658 LXVII1.-Constituents of the Indian Dyestuff Waras, PZemingia congsstcc. By ARTHUR GEORGE PERKIN, F.K.S.E. . . . 659 LX1X.-Azobenzene Derivatives of some Natural Yellow Colouring Matters : Apigenin, Chrysin, Morin, Euxanthone, and Gentisin. By ARTHUR GEORGE PERKIN, F.R.S.E. . 665 LXX.-The Vapour Presures, Specific Volumes, and Critical Constants of Normal Heptane. By SYDNEY YOUNG, D.Sc., LXX1.-Contributions to the Chemistry of Phenol Derivatives. By RAPHAEL MELDOLA, F.R.S., and FREDERICK HENRY STREATFEILD . . . . . . . . . . 68 1 LXXI1.-Some Iodoso-compounds.By JOHN MCCRAE, Ph.D. . 691 LXXIT.1.-Notes on the Absorption Bands in the Spectrum of By W. N. HARTLEY, F.R.S., and J. J. DOBBIE, LXX1V.--On Myrticolorin, the Yellow Dye Material of LXXV.-Chemical Properties of Concentrated Solutions of Certain Salts. Part 11. Double Potassium Succinates. By WILLIAM COLEBROOK REYNOLDS, A.R.G.S. , . , , 701 Halogen Deriva- tives of Fenchone and their Reactions. By JOHN ADDYMAN GARDNER, M.A., and GEORGE BERTRAM COCKBURN, B.A. . 704 On the Oxidation of Fenchone. By JOHN ADDYMAN GARDNER, M.A., and GEORCIE BERTRAM COCKBURN, B.A. . . . . . 7 0 8 LXXVIIL-Riintgen Ray Photography applied t o Alloys. By CHARLES THOMAS HEYCOCK and FRANCIS HENRY NEVILLE . 714 LXX1X.-A dditive Compounds of Organic Bases and Etherezl Salts of Unsaturated Acids.By S. RUHEMANN, Ph.D., M.A., and K. 0. BROWNING . . . . . . . 723 Chain Carbon Compounds. and J. J. DOBBIE, M.A., D.Sc. . . . . . . 5 9 8 and WILLIAM JACKSON POPE: . . . . . . . 606 and JOHN K. WOOD . . . . . . . . . 618 By FRANK GEORGE EDMED, B.Sc., A.R.C.S. . . . . 627 HILL, B.A. . . . . . . . . . . . 634 F.R.S., University College, Bristol . . . . . 676 Benzene. M.A., D.Sc. . . . . . . . . . . 6 9 5 Eucalyptus Leaves. By HENRY G. SMITH . . . . 697 LXXV1.-Researches on the Terpenes, 111. LXXV1I.-Researches on the Terpenes, IV.... V l l l CONTENTS. LXXX.-Formation of Ethereal Salts of P-Ketonic Acids. By s. ~ H E M A N N , Ph.D., M.A., and K. C. BROWNING, B.A. . LXXX1.-Disulphonic Acids of Toluene, of Ortho- and Para- toluidine, and of Ortho- and Para-chlorotoluene.By W. PALMER WYNNE, D.Sc., F.R.S., and JAMES BRUCE, B.Sc. , LXXXI1.-The Chlorine Derivatives of Pyridine. Part 11. Interaction of Ammonia and Pentachloropyridine. Con- stitution of Glutazine. By W. T. SELL, M.A., F.I.C., and F. W. DOOTSON, M.A. LXXXIJ.1.-Mercury Acetamide. By MARTIN ONSLOW FORSTER, Ph.D., B.Sc. . LXXX1V.-Sul phocamphylic Acid and Isolauronolic Acid, with Remarks on the Constitution of Camphor and of some of its Derivatives. LXXXV.-Researches on the Terpenes. VIII. On Carvenol : its Reactions and Products. By J. E. MARSH and A. HARTRIDGE . LXXXVI. -Optically Active Alkyloxypropionic Acids. By THOMAS PURDIE, F.R.S., and G, DRUCE LANDER, B.Sc. LXXXVII .-Optical Activity of Gallotsnnic Acid. By OTTO ROSENHEIM, Ph.D., and PHILIP SCHIDROWITZ, Ph.D.LXXXVIII. -The Influences Modifying the Specific Rotatory Power of Gallotannic Acid. By OTTO ROSENHEIM, Ph.D., and PHILIP SCHIDROWITZ, Ph.D. LXXX1X.-The Resolution of Tetrahydropapaverine into its Optically Active Components. Constitution of Papaverine. By WILLIAM JACKSON POPE and STANLEY JOHN PEACHEY . XC.-The non-Resolution of Racemic Tetrahydropapaverine by Tartaric Acid. By WILLIAM JACKSON POPE and STANLEY JOHN PEACHEY . XCL-Composition of American Petroleum. By SYDNEY YOUNG, D.Sc., F.R.S. . XCI 1,-Separation of Normal and Iso-heptane from American Petroleum. By FRANCIS E. FRANCIS, B.Sc., Ph.D., and SYDNEY YOUNG, D.Sc., F.R.S. . XCII1.-Specific Gravities and Boiling Points of Mixtures of Benzene and Normal Hexane. By D. HAMILTON JACKSON, M.A., B.Sc., Ph.D., and SYDNEY YOUNQ, D.Sc., F.R.S. XC1V.-Action of Fuming Nitric Acid on the Paraffins and other Hydrocarbons. By FRANCIS E.FRANCIS, B.Sc., Ph.D., and SYDNEY YOUNQ, D.Sc., F.R.S. . XCV.-Hexamethylene from American and Galician Petroleum. By EMILY C. FORTEY, B.Sc. XCV1.-A Composite Sodium Chlorate Crystal in which the Twin Law is not followed. By W~LLIAM JACKSON POPE . By W. H. PERKIN, jun. . . PAGE 727 730 777 783 796 852 862 878 885 893 902 905 920 922 928 932 949CONTENTS. ix PAGE XCVI1.-Contributions t o the Chemistry of Thorium ; Com- parative Research on the Oxalates of the Rare Earth. By BOHUSLAV BRAUNER, Ph.D., Professor of Chemistry in the Bohemian University, late Berkeley Fellow of Owens College XCVII1.-Studies of the Terpenes and Allied Compounds.Nitrocamphor and its Derivatives. I. Stereoisomeric Chloro- and Bromo-nitrocamphors. 11. Pseudo-nitro- camphor. 111. Camphoryloxime (Camphonitrophenol). By T. MARTIN LOWRY, B.Sc. . . 986 XCIX-Formation of Ethereal Salts of Polycarboxylic Acids. By S. RUHEMANN, Ph.D., M.A., and A. V. CUNNINGTON, B.A., Scholar of Christ’s College . . 1006 C.-Yellow Colouring Principles contained in various Tannin Matters. Part VI. Rhus Cotinus and Rhus Rhodanthemcc. By A. G. PERKIN, F.R.S.E. . . 1016 C1.-Golouring Matters of the New Zealand Dyewood Puriri, C1I.-Derivatives of Hesperitin. By A. G. PERKIN, F.R.S.E. . 1031 Anniversary Meeting . . 1039 Obituaries . 1047 951 Vitex littoral&. Part I. By A. G. PERKIN, F.R.S.E. . 1019CONTENTS. ix PAGE XCVI1.-Contributions t o the Chemistry of Thorium ; Com- parative Research on the Oxalates of the Rare Earth. By BOHUSLAV BRAUNER, Ph.D., Professor of Chemistry in the Bohemian University, late Berkeley Fellow of Owens College XCVII1.-Studies of the Terpenes and Allied Compounds. Nitrocamphor and its Derivatives. I. Stereoisomeric Chloro- and Bromo-nitrocamphors. 11. Pseudo-nitro- camphor. 111. Camphoryloxime (Camphonitrophenol). By T. MARTIN LOWRY, B.Sc. . . 986 XCIX-Formation of Ethereal Salts of Polycarboxylic Acids. By S. RUHEMANN, Ph.D., M.A., and A. V. CUNNINGTON, B.A., Scholar of Christ’s College . . 1006 C.-Yellow Colouring Principles contained in various Tannin Matters. Part VI. Rhus Cotinus and Rhus Rhodanthemcc. By A. G. PERKIN, F.R.S.E. . . 1016 C1.-Golouring Matters of the New Zealand Dyewood Puriri, C1I.-Derivatives of Hesperitin. By A. G. PERKIN, F.R.S.E. . 1031 Anniversary Meeting . . 1039 Obituaries . 1047 951 Vitex littoral&. Part I. By A. G. PERKIN, F.R.S.E. . 1019