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Molecular Organic Compounds of Ortho and Para Aminobenzoic Acids

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Molecular Organic Compounds of Ortho and Para Aminobenzoic Acids University of Tennessee, Knoxville TRACE: Tennessee Research and Creative Exchange Masters Theses Graduate School 8-1932 Molecular Organic Compounds of Ortho and Para Aminobenzoic Acids Weldon E. Cate University of Tennessee - Knoxville Follow this and additional works at: https://trace.tennessee.edu/utk_gradthes Part of the Chemistry Commons, and the Education Commons Recommended Citation Cate, Weldon E., "Molecular Organic Compounds of Ortho and Para Aminobenzoic Acids. " Master's Thesis, University of Tennessee, 1932. https://trace.tennessee.edu/utk_gradthes/3230 This Thesis is brought to you for free and open access by the Graduate School at TRACE: Tennessee Research and Creative Exchange. It has been accepted for inclusion in Masters Theses by an authorized administrator of TRACE: Tennessee Research and Creative Exchange. For more information, please contact [email protected]. To the Graduate Council: I am submitting herewith a thesis written by Weldon E. Cate entitled "Molecular Organic Compounds of Ortho and Para Aminobenzoic Acids." I have examined the final electronic copy of this thesis for form and content and recommend that it be accepted in partial fulfillment of the requirements for the degree of Master of Science, with a major in Education. Calvin A. Buehler, Major Professor We have read this thesis and recommend its acceptance: ARRAY(0x7f6ffe369bd8) Accepted for the Council: Carolyn R. Hodges Vice Provost and Dean of the Graduate School (Original signatures are on file with official studentecor r ds.) July 11, 1932 31> "To The Committee on Gra.dua ta Stuclya I submit herewith. a. thesis 'by ar •.Veldon E\lg�ne Ca.te• "M�oul� Or·gjmic aompounas of Ortho and Para. .Aminoben�bic Acids"• a.:nd: recommend that it be aooepted tor 81ghteen (18) qU!U"ter hours credit in :f'ultillment ot the ret�Uirements for the degree ot Master or Soienoe in Eduoatione At the request of the Commit tee on Graduate Study, I have re ad this thesis and re commend its acceptance. �ept.O by the Committee �-�� Chairman MOLECULAR ORGANIC COMPOUNDS OF ORTHO AND PARA �NOBENZOIC ACIDS A THESIS Submitted to the Graduate Committee .. ··.·. ot .. The University of Tennessee ... .. .. ... in .... Partial Fulfillme nt of the Requirements for the Degree of Master of Science in Education WELDON E. CATE August,l932 ii. ACKNOWLEDGEMENT I wish to express my deepest appreciation to Dr . Calvin A. Buehler for his kindly criti­ cism and guidan ce throughout this investigation. I also wish to acknowledge the cooperation and interest shown by Miss Mildred Gallaher while typing the manuscri·pt. iii. TABLE OF CONTENTS Chapter Page I. INTRODUCTION . 1. II. HISTORICAL PART . 3. III. EXPERIMENTAL PART. 10. • Preparation of First Components • • • • • • 10. o-Aminobenzoic Acid •• •••• ••••• ••• 10. p-.Aminobenzoic Acid • • • • • • • • • • • • • • 11. Preparation of Organic Molecular Compounds •• • • 12. Second Components • • • • • • • • • . • . 12. Methods of Preparation and Purification • • 13. Solution Method • • • • • • • • • • • • • • • 13. • • • . Fusion Method • • . • • . 15. Concentration-Freezing-Point Cur�s ••• . 16. Determination of Physical Properties ••• • • 69. Determination of Melting Points • • • • . 69 . Determinat ion of Neutral Equivalents. • • • • 70. �alysis of Molecular Compounds • • • • • . • 73. • • • • IV. THEORETICAL DISCUSSION • • • • 77. Theories of Valence • • • • • • • • • • • • • • 77. • • • Thegry of Principal Valence • • • • • • 77. Theory of Subsidiary Valence. • • • . • • • • 78. The Electronic Theory • • • • • • • • • • • • 79 . Probable Structure of the Organic Molecular Compounds • • • • 83 . v. SUMMARY • • • • • • • • • • • • • • • • • • 86 . BIBLIOGRAPHY. 87 . iv. LIST OF TABLES Table Page Concentration-Freezing-Point Data of the Following Binary Solutions: l. o-Aminobenzo ic Acid and .l.cetamide • . 19 . 2. o-Aminobenzoi c Acid and Aniline • • • . • • 21 • 3. o -Aminobenzoi c Acid and DimehQylani line • • . • 23 . 4. o-Am inobenzoi c Acid and Methylaniline . • . • 25 . 5. o-Aminobenzoi c Acid and a-Naphthylamine • . • • 27. 6. o-Am inobenzoic Aci d and o-Phenylenediamine . 29. 7. o -Amino benzo 1 c Acid and m-Phenylenediamine . • • 31 . a. o-Ami nobenzoi c Acid and Pyridine • • . • . 33 . 9. o-Aminobenzoi c Acid and o-Toluidine • • • • • 35. 10 . o-Aminobenzof c Aci d and 11-Toluidine • . • • • • 37 . 11. o-Aminobenzoi c Acid and p-Toluidine • • • • • . 39 . 12 . o-Aminobenzo ic Ac.id and Triethylamine • • • • • 42 . 13. p-Aminobenzoic Acid and Acet amide • • • • • . • 44 . 14 . p·Amino benzol c Acid and b!l:tpe • .. • • . • . • 46 . 15 . p-Am inobenzoic Acid and Diethylamine. • • 49 . 16 . p-Aminobenzoi c Acid and Dimethylaniline • • • • 51 . 17. p-Aminobenzoi c Acid and Methylaniline • . • 53 . 18 . p-Aminobenzoi c Acid and a-Naphthylamine • . • • 55. 19 . p-Aminobenzoi c Acid and o-Phenylenediamine . • • 57 . 20. p-Aminobenzoi c Acid and m-Phenylenediamine . • • 59 • v. Table Page 21 . p-Aminobenzo i c Aci d and Py ri dine • • • • • • • • 61 • 22. p-Aminobenzoic Acid and o-Toluidine • . • . 63 • 23 . p-Aminobenzoi c Acid and m-Toluidine • • • • . • 65 • 24 . p-Aminobenzoic Acid and p-Toluidine • • . • . • 67 . 25. Physical Properties of the Molecular Com - pounds of o�inobenzoic Acid • • • . • . • 71 • 26 . PhJB ical Properti es or the Molecular Com- pounds or p-Am inobenzoi c Acid • • • • .. • . • 72• 27. Analytical Resul ts on the Molecular Com - pounds of o-Aminobenzoi c Acid • • • • • • . • 75 . 28. Analytical Resul ts on the Molecular Com - pounds of p�inobenzoic Ac id • • • • • . • • 76. LIST OF ILLUSTRATIONS Illu stration Page Concentration-Fre ezing-Point Curves of the Following Binary So lutions: 1. o-Aminobenz oi c Acid and Acetamide • . • . • . • 20 • 2. o-Aminobenzoi c Acid and Aniline • • • • . • • 22 • 3. a-Aminobenzo ic Ac id and Di me thylaniline • • • • 24 • 4. a-Aminobenzoic Aci d and Methylaniline • • . • 26. 5. o-Aminobenzoic Acid and a-Naphthylamine • • . • 28. 6. o-Aminobenzoi c Acid and a-Phenylenediamine . • • 30 . 7. a-Aminobenzoic Acid and m-Phenylenediamine . • • 32 . a. a-Aminobenzo ic Acid and. Pyridine • . • . • 34. 9. a-Aminobenz oic Acid and o-Toluidine • • • • • 36 . 10. o-Aminobenzoi c Acid and m-Toluidine • • • • • • 38 • 11 . o-Aminoben z a1. c Acid and p-Toluidine • • • . • 40 • 12. o-Aminobenzoic Acid and Tri ethylamine • • . • 43 . 13. o-Aminobenzo ic Acid an d Acetamide • • • • • . • 45 . 14:. p·Aminobenzol c Acid and Allillpe '• · .• • • . • 47. 15 . p-Aminobenzoic Acid and Diethylamine • • • . • 50 • 16. p-Aminobenzoi c Acid and Dimethylaniline • . • 52 • 17. p-Aminobenzo ic Ac id and Methylaniline • • . • • &4 • 18. p-Aminobenzoi c Acid and a-Naphthylamine • • . • 56 . 19. p-Aminobenzoi c Acid and a-Phenylenedi amine . • • 58 • vi i. Illustration Page 20. p-Aminobenzo i c Acid and m-Phenylenediamine • 60 • 21. p-Aminobenzo ic Acid and Pyridine • • • . • • 62 • 22. p-Aminobenzoi c Acid and·o -Toluidin e • . • 64 • 23. p-Aminobenzo ic Acid and m-Toluidine • . 66 • 24. p-Aminobenzoi c Acid and p-Toluidine • . 68 • Chapter I INTRODUCTION The nature of the linkage between the components of molecular organic compounds is not clearly understood, al­ though the existence of this type of compound has been known for many years. Since efforts to explain the struc­ ture of molecular compounds by the different theories of valence have met with only partial syccess, a series of investigations is being carried out in the Chemistry Labo­ ratories of the University of Tennessee in an effort to formulate a theory by which the structure and properties ot this interesting but perplexing type of compound may be explained. The object of this investigation of the molecular organic compounds of the o- and p-aminobenzoic acids is to add to the data which is being collected in this labora­ tory with the hope that a sufficient amount of information will lead to a conclusive explanation of the linkage between the components of molecular compounds. It is also thought that by determining the additive nature of o-aminobenzoic acid it will be possible to pre­ dict the possibility of a chelate ring structure which is characteristic of a large number of ortho disubstituted 2. benzene derivatives. The procedure being followed in th is inve stigation is much th e same as that of precedi ng investigations wh ich have be en carried out in th is laboratory on molecular or­ ganic compounds. The general procedure may be outlined as follows: 1. To make a survey of all available literature and collect data on all mo lecular organic compounds of th e o­ and p-am inobenzoic acids whi ch have been prepared by other investigators. 2. To prepare mo lecular compounds of th e o- and p­ aminobenzoic acids with a number of amines, phenols , and hydrocarbons . 3. To determine the melting points , color, and neutral equivalents of th e compounds prepared and check them �gainst th ose found in th e lite rature . 4. To determine by an�lysis th e mo lecular ratios existing in th e compounds prepare d. 5. To consider th e structure of th ese compounds and try to explain th e nature of the linkage exi s ting between th e components . Chapter II HISTORICAL PART1 A number or molecular organi c compounds of o- and p­ aminobenzoic acid have been obtained by different inves ­ tigators bu t no evidence was found in the literature searched of a thorough investigation of these compounds . 2 In 1908 Pawlewski obtained a mole cular compound of o-aminobenzoic acid with p-dimethylaminobenzaldehyde by grinding the two components together and moistening
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