J O U R N A L OF THE CHEMICAL SOCIETY. TRANSACTIONS. A. UHASTON CHAPMAN. A.W. CROSSLEY,C.M.G.,D.SC.,F.R.S. M. 0. FOWI'ER D.Sc. Ph.I). F.K.S. A. HARDEN DSc. Ph.D. P.R.S. T. A. HENRY D.Sc. '1'. M. LOWRY O.R.E D.Sc. F.R.S. J. C. PHILIP D.Sc. Ph.D. W. J. PoPE,C.B.E.,M.A.,D.SC.,F.R.S. F. L. PYMAN D.Sc. Ph.D. A . SCOTT M.A. D.Sc. F.R.P. G. SENTER D.Yc. Ph.D. S. SMILES D.Sc. J. F. THORPE C.B.E. D.Sc. Ph.D., F.R.S. $bifor : J. C. CAIN D.Sc. Ph.D. Su&-&fibitax : A. J. GREENAWAY. 2,bsisfLtirt Sub.-@&itar : CLABEX'CE SMITH D. Sc. 1917 Vol. CXI. Part I. pp. 1-588. LONDON: GURNEY & JACKSON 33 PATERNOSTER ROW E.C. 191 7 PRINTED IN GREAT BRITAIN BY RICHARD CLAY & SONS LIB~ITED, BRUNSWICK ST. STAMFORD ST. 9.E. 1, AND BUNGAY SUFFOLK CONTENTS.PAPERS COMMUNICATED TO THE CHEMICAL SOCIETY. PAGE 1.-Studies in Ring Formation. Part 11. The Action of Aromatic Amines on Acetylacetone and Renzoylacetone. I I .-T he 8 y n t’hesis of Hydrox y quercetin. By MAXIM I LIAN KIERESSTEIN . 111.-The Friedel-Crafts’ Reaction. Part I. Phthalyl Chloride and the Mechanisni of its Reaction with Benzene. By MAURICE COPISAROW . 1V.-The Resolution of Asymmetric Quinquevalent Nitrogen Compounds. Part I. The Salts of d- and I-Phenylbenzyl-methylallylammonium Hydroxide with cl- and I-a-Brotno-camphor-rr-sulphonic Acid. By JOSEPH REILLY . . V.-Lead Subiodide and an Improved Method for Preparing Lead Suboxide. The Solubility of Lead Iodide. By HENRY GEORGE DENHAM , V1.-The Displacement of Sulphonic Acid Groups in Amino-sulphonic Acids by Halogen A4toms.By JOHN JOSEPH SUDBOROUGH and JAMIAT VISHINDAS LAKHUMALANI VI1.-Xelationship between the Physical Properties of Isomeric Cobaltammines and the Electro-valencies of their Co-ordination Complexes. By RAJENDRA LAL De . VII1.-Spinacene A New Hydrocarbon from certain Fish Liver oils. By A. CHASTON CHAPMAN . 1X.-The Nitration of 2-Acetylamino-3 4-dimethoxybenzoic Acid and 3-Acetylaminoveratrole. By CHARLES STANLEY GIBSON JOHN LIONEL SIMONSEN and MADYAR GOPALA RAU . X.-The Detergent Action of Soap. By SPENCER UMFREVILLE PICKERING . XI.-Mercury Mercapticle Nitrites and their Reaction with the Alkyl Iodides. P a r t 111. Chain Compounds of Sulphur. By PRAFULLA CHANDRA RAY . By EUSTACE EBENEZER ‘FCJRNER .. 1 4 10 20 29 41 51 56 69 86 101 XIL-Azoxycatechol Ethers and Related Substances. By GERTRUDE MAUD ROBINSON . . 109 XII1.-Evidence of the Existence i n Malt of an Enzyme Hydrolysing the Furfuroids of Barley. By JULIAN LEVETT BAKER and HENRY FRANCIS EVERARD HULTON . 121 X1V.-“ Stepped ” Ignition. By RICEIARD VERNON WHEELER . 130 XV.-Studies of the Carbonates. Part 11. Hydrolysis of Sodium Carbonate and Bicarbonate and the Ionisation Constants of Carbonic Acid. By CLARENCE ARTHUR SEYLER and PERCY VIVIAN LLOYD . . 13 iv CONTENTS. PAGE XV1.-Cadmium and Zinc Nitrites. By PRAFULLA CHANDRA RAY . . 159 XVI1.-Notes on the Effect of Heat and Oxidation on Linseed Oil. By JOHN ALBERT NEWTON FRIEND . . 162 XV1II.-Relation between Chemical Constitution and Physio-logical Action in Certain Substituted Aminoalkyl Esters.Part 11. By FRANK LEE PYMAN . . 167 X1X.-Boric Anhydride and its Hydrates. By JAMES ECKERSLEY MYERS . . 172 XX.-A Simple Apparahus for the Washing of Gases. By HAROLD HEATII GRAY. . 179 XX1.-Solvent Effect and Beer’s Law. By ALFRED WALTER STEWART and ROBERT WRIGHT . 183 XXI1.-Acyl Derivatives of Paradiazoiminobenzene. By GILBERT T. MORGAN and ADOLPH WILLIAM HENRY UPTON . 187 XXII1.-Chromium Phosphate. By ALFRED FRANCIS JOSEPH and WILLIAM NORMAN EAE . . . . 196 SOME MAIN LINES OF ADVANCE IN THE DOMAIN OF MODERN ANALYTICAL CHEMISTRY. A Lecture delivered before the Chemical Society on March 19th 1917. By A. CHASTON CHAPMAN . . 203 XX1V.-The Nitration of Isomeric Acetylaminoi~~ethoxybenzoic Acids.By JOHN LIONEL SIMONSEN and MADYAR GOPALA I<AU . . 220 XXV.-The Detection of Traces of Mercury Salts for Toxico-logical Purposes. By KERTDALL COLIN BROWNIKG . . 236 XXV1.-The Action of Bromine Water on Ethylene. By JOHN READ and MARGARET MARY WILLIAMS . . 240 XXVT1.-Trimethyl Glucose from Cellulose. By WILLIAM SMITH DENHAM and HILDA WOODHOUSE . . 244 XXVII1.-The Le Chntelier-Brmu Principle. By LORD RAYLEIGH O.M. . 250 XXIX.-The Structure of Inorganic Compounds. By SAMUEL HENRY CLIFFORD BRIGGS . . 253 XXX.-The Propagation of Flame in Mixtures of Acetone and Air. By RICRARD VERNON WHEELER and ARNOLD WHITAKER . . 267 ANNUAL GENERAL MEETIXG . . 273 PRESIDENTIAL ADDRESS . . 288 OBITUARY N~TICES . . 312 XXX1.-The Action of Sulphur Dioxide on Metal Oxides.Part I. By DALZIELLEWELLYN HANMICK . 37 CONTENTS. V PAUR XXXI1.-Studies in Catalysis. Part VI. The Mutual Influence of two Reactions Proceeding in the Same Medium. By ROBERT OWEN GRIFFITH ALFRED LAMBLE and WILLIAM CUDMORE MCCULLAGH LEWIS . 389 XXXII1.-The Properties and Constitution of some New Basic Salts of Zirconium. By ERNEST HARRY RODD . . 396 XXX1V.-Methyl Nonyl Ketone from Palm Kernel Oil. By ARTHUR HENRY SALWAY . . 407 XXXV.-The Infliience of Pressure on the Ignition of a Mixture of Methane and Air by the Impulsive Electrical Discharge. By RICHARD VERNON WHEELER . . . 411 XXXVL-Velocity of Decomposition and the Dissociation Con-stant of Nitrous Acid. By PRAFULLLA CHANDRA RAY, MANIK LAL DEP and JNANENDRA CHANDRA GHOSH .. 413 XXXVIL-A Simple Method of Preparing Potassium Stanni-chloride. By JOHN GERALD FREDERICK DRUCE . . 418 XXXVXI1.-The Alkaloids of Ipecncuanha. Part 11. By FRANK LEEPYMAN . . 419 XXX1X.-Studies on the Walden Inversion. Part P. The Kinetics and Dissociation Constant of P-Phenyl-a-bromo-propionic Acid. By GEORGE SENTER and GERALD HARGRAVE MARTIN . . . . 447 XL.-Studies in Catalysis. Part VII. Heat of Reaction, Equilibrium Constant and Allied Quantities from the Point of View of the Radiation Hypothesis. By WILLIAM CUDMORE MCCULLAGB LEWIS . . 457 XLI-The Hydration of Ions and Metal Overvoltage. By EDGAR NEWBERY . . 470 XLI1.-The Crystal Form and Isomerisin of Some Ferro-XLII1.-Compounds of Calcium Chloride and Acetone. By LANCELOT SALISBURY RAGSTER .. 494 XL1V.-The Constitution of Internal Diazo-oxides (Diazo-phenols). Part 11. Hy GILBERT T. MORGAN and HENRY PHILIP TOMLINS . . . 497 XLV.-Alkaloidal Derivatives of Mercuric Nitrite By PRAFULLA CHANDRA R l i ~ . . 507 XLV1.-Synthesis of ap-Thiocrotonic Acid. By PRAFULLA CHANURA RAY and MANIK LAL DEY . . 510 XLVII. -Studies in the Phenylsuccinic Acid Series. Part IV. The I-Menthyl Esters of the Diphenylsuccinic Acids. By HENRY WREN and CHARLES JAMES STILT . . 513 XLVII I. -At temp t s t o Prepare Asy tnme tric Quinquevalent Nitrogen Compounds. Part I. 5-Aminosalicylic Acid and Related Compounds. By (the late) RAPHAEL MELDOLA, cyanides. By GEORGE MACDONALD BENNETT . . 490 HENRY STENNETT FOSTER and RAINALD BRIGETMAN . . 53 vi CONTENTS.XL1X.-Attempts to Prepare Asymmetric Quinquevalent Nitrogen Compounds. Part 11. Nitrated Hydroxydi-phenylmines. By (the late) RAPHAEL MELCOLA HENRY L.-Attempts t o prepare A symmetric Quinquevalent Nitrogen Compounds. Part 111. Hydroxyphenylglycine. By (the late) RAPEAEL MELDOLA HENRY STENNETT FOSTER and RAINALD BRIGHTMAN . STENNETT FOSTER and RAINALD BRIGHTMAN . . L1.-The Constitution of Cyanamide. By EMILE COLSON . LI1.-Separation of Secondary Arylamines from Primary OBITUARY NOTICE . LII1.-Contributions to the Chemistry of Caramel. Part I. Caramelan. By MARY CUNNINGHAM and CRARLES DORI~E . L1V.-Action of Acetaldehydeammonia on Quinones. By PRAPHULLA CHANDRA G H ~ S H . LV.-'l'he Conversion of o-Nitroamines into isoOxadiazole Oxides and of o-Nitrosoamines into isoOxadiazoles.By ARTHUR G. GREEN and FREDERICK MAURICE ROWE . . LV1.-The Phosphates of Calcium. Part IV. The Basic Phcsphates. By HENRY BASSETT jun. LVII.-(' Spark-Lengths " in Various Gases and Vapoure. By ROBERT WRIGHT . LVII1.-Constitution of the Salts of XAlkylthiocarbamides. By JOHNTAYLOR . . . . . . L1X.-Phosphorescent Zinc Sulphide. By ELIZABETH MAC-DOUGALL ALFRED WALTER STEWART and ROBERT WRIGHT . LX.-Salts of Thiocarbamide. By AUGUSTUS EDWARD DIXOS . LX1.-Catalysis. P a r t 111. Some Induced Reactions. By LXI1.-Catalysis. Part IV. Temperature Coefficients of LXII1.-A Synthesis of Tropinone. Ey ROBERT ROBINSON . LX1V.-The Pungent Principles of Ginger. Part I. A New Ketone Zingerone (4-Hydroxy-3-methoxyphenylethyl Methyl Ketone) occurring in Ginger.By HIROSHI NOMURA LXV.-The Pungent Principle of Ginger. Part I. The Chemical Characters and Decomposition Products of Thresh's '( Gingerol." By ARTHUR LAPWORTH (MRs.) LEONORE KLEI z PEARSON and FRANK ALBERT ROYLE . LXV1.-The Pungent Principles of Ginger. Part 11. Synthetic Preparations of Zingerone Methylzingerone and some Related Acids By ARTHUR LAPWORTH and FREDERICK HENRY WYKES . Amines. By JOHN THOMAS . NILRATAN DHAB. . Catalysed Reactions. By NILRATAN DHAR . YAGE 546 55 1 554 562 572 589 608 612 620 643 650 663 684 690 707 762 769 777 79 CONTENTS vii PAGE LX VIL-The Determination of Ozone and Oxides of Nitrogen in the Atmosphere. By FRANCIS LAWRY USHER and BASRUR SANJIVARAO . LXVII1.-Compounds of Ferric Chloride with Ether and with Dibenzyl Sulphide.By AQUILA FORSTER CHRISTOPHER COOPER and GEORGE YARROW , LX1X.-The Effect of Additional Auxochromes on the Colour of Dyes. Part T I . Triphenylmethane and Azo-dyes. By PRAPHULLA CHANDRA GHOSH and EDWJN ROY WATSON . LXX.-The Absorption Spectra of Substances containing Con-jugated and Unconjugated Systems of Triple Bonds. By ALEXANDER KILLEN MACBETH and ALFRED WALTER STEWART . LXX1.-The Uniform Movement of Flame in Mixtures of Acetylene and Air. By WILLIAM ARTHUR HAWARD and SOSALE GARALAPURY SASTRY . Part I. The Mechanism of the Interaction of Formaldehyde and Ammonium Chloride ; the Preparation of Methylamine and of Dimethylamine. By EHIL ALPHONSE WERNER . LXXIIL-The Liberation of Hydrogen Sulphide from Gob Fires in Coal Mines.By THOMAS JAMES DRAKELEY . LXX1V.-The Constitution of Carbamides. Part IV. The Mechanism of the Interaction of Urea and Nitrous Acid, LXXV.-A Theory of the Mechanism of the Phytochemical Synthesis of certain Alkaloids. By ROBERT ROBIXSON . LXXV1.-Reduction of Aliphatic Nitrites to Amines. By PANCHANAN NEOGI and TARINI CHARAN CHOWDHURI . LXXVI1.-Experiments on the Orientation of Substituted Catechol Ethers. By THOMAS GILBERT HENRY JONES and ROBERT ROBINSON . LXXVII1.-The Scission of Certain Substituted Cyclic Catechol Ethers. By GERTUDE MAUD ROBINSON and ROBERT ROBINSON . . . By ELLEN MARGARET HINDMARSH ISABEL KNIGHT and ROBERT ROBINSON . By ANNIE MARY BLEAKLY ORR ROBERT ROBINSON and MARGARET MARY WILLIAMS .LXXXI. -Veratricsulphinide. By JANET FORREST MCGILLIVRAY BROWN and ROBERT ROBINSON . LXXXI1.-Researches on Pseudo-bases. Part 11. Note on some Berberine Derivatives and Remarks on the Mechanism of the Condensation Reactions of Pseudo-bases. By GERTRUDE MAUD ROBINSON and ROBERT RORINSQN LSXI1.-Methylation by Means of Formaldehyde. By EMIL ALPHONSE WERNER . . . LXXIX.-5-Bromoguaiacol and some Derivatives. LXXX.-The Action of Halogens on Piperonal. . 799 80'3 815 829 841 8 44 s53 863 876 899 903 929 940 946 952 95 ... V l l l CONTENTS PAQE LXXXII1.-The Absorption Spectra of some Polyhydroxy-anthraquinone Dyes in Concentrated Sulphuric Acid Solu-tion and in the State of Vapour. By DAVID B. MEEK . 969 LXXX1V.-Action of Phenylhydrazine on Opianic Nitro-opianic and Phthalonic Acids Some Derivatives of Hydrazo- and Azo-phthalide.By PRAFULLA CHANDRA MITTER and JNAKENDRA NATH SEN . . 985 LXXXV.-Studies of the Carbonates. Part 111. Lithium, Calcium and Magnesium Carbonates. By CLARENCE ARTHUR SEYLER and PERCY VIVIAN LLOYD . . 994 INTERNATIONAL ATOMIC WEIGHTS . . 1001 LXXXV1.-The Temperature of Ignition of Gaseous Mixtures. By JAMES WALLACE MCDAVID . . 1003 LXXXVI1.-Disodium Nitrite an Additive Compound of Sodium Nitrite and Sodium. By EDWARD BRADFORD MAXTED . . 1016 LXXXVIX1.-Studies in the Phenylsuccinic Acid Series. Part V. The Inter-conversion of the Esters of r- and meso-Diphenylsuccinic Acids. By HENRY WREN and CHARLES JAMES STILL . 1019 LXXX1X.-Derivatives of n-Butylauiline. By JOSEPH REILLY and WILFRID JOHN HICKINBOTTOM . . 1026 XC.-The Limitations of the Balance. By EERTRAM BLOUNT 1035 XCL-3 4-Di-p-nitrotetraphenylfuran. By ARTHUR GORDON FRANCIS . . 1039 XCI1.-The (‘ Uniform Movement ” during the Propagation of Flame. By WALTER MASON and RICHARD VERNON WHEELER 1044 XC1II.-The Hydrolysis of Sodiuin Cyanide. By FREDERICK PALLISER WORLEY and VERE ROCHELLE BROWNE . 1057 XC1V.-The Polysulphides of the Alkali Metals. Part 111. The Solidifying Points of the Systems Sodium Mono-sulphide-Sulphur and Potassium Monosulphide-Sulphur. By JOHN SMEATH THOMAS and ALEXANDER RULE . XCV.-Studies in Catalysis. Part VJ 11. Thermochemical Data and the Quantum Theory. High Temperature Xeactions. Ey WILLIAM CUDMORE MCCULLAGH LEWIS. . . 1086 THE RELATION BETWEEN CHEMICAL COXSTITUTION AND PHYSIO-LOGICAL ACTION. A Lecture delivered before the Chemical Society on December 6th 1917. . . 1063 By FRANK LEE PYMAN. ‘110