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University Microfilms, a XEROX Company, Ann Arbor, Michigan 71- 12,571 lAl'S:::, Barbara lelen, 193S- Ï. ILEGTROCIEIICAL CXIDATIC" OF FICLOGICALLY lEPORTAET XARTHIRES. II. ELECTROCIZIIGAL REDUCTICR OF ALLOXAN, NLTHYL- AND DIMETHYL ALLOXAN IN AQUEOUS AND AGLTONITRILZ SOLUTIONS. The University of Ohlahcrs, I'h.T., 1970 Cheristry, analytical University Microfilms, A XEROX Company, Ann Arbor, Michigan THIS DISSERTATION HAS BEEN MICROFILMED EXACTLY AS RECEIVED THE UNIVERSITY OF OKLAHOMA GRADUATE COLLEGE I. ELECTROCHEMICAL OXIDATION OF BIOLOGICALLY IMPORTANT XANTHINES II. ELECTROCHEMICAL REDUCTION OF ALLOXAN, METHYL- AND DIMETHYL ALLOXAN IN AQUEOUS AND ACETONITRILE SOLUTIONS A DISSERTATION SUBtllTTED TO THE GRADUATE FACULTY in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY BY BARBARA. HELEN HANSEN Norman, Oklahoma 1970 I. ELECTROCHEMICAL OXIDATION OF BIOLOGICALLY IMPORTANT XANTHINES II. ELECTROCHEMICAL REDUCTION OF ALLOXAN, METHYL- AND DIMETHYL ALLOXAN IN AQUEOUS AND ACETONITRILE SOLUTIONS APPROVED BY DISSERTATION COMMITTEE DEDICATION To the many, beginning with my parents, who have entered my life and by the Spirit of their lives have strengthened faith, renewed hope and taught love: "And man the stumbler and finder, goes on, man the dreamer of deep dreams, man the shaper and maker, man the answerer."* *Lines from "Man will never write" by Carl Sandburg. iii ACKNOWLEDGEMENTS The authoress is most indebted to Dr. Glenn Dryhurst, who sug­ gested these problems, for his counsel and assistance during the course of this research and in the preparation of this manuscript. Financial assistance given by the National Aeronautics and Space Administration as a Training Grant through the auspices of the University of Oklahoma (NGT 37-003-001) during three years of graduate study and for partial support by National Science Foundation through Grant No. GP 8151 awarded to Dr. Dryhurst is gratefully acknowledged. Acknowledgement of the guidance of the late Dr. Harold E. Affsprung in my earliest research ventures and of Dr. Sherrill D. Christian for his assistance during the difficult interim between research directors is given with gratitude. The assistance of Mr. Carl Starkey, Mr. Ron Stermer and es­ pecially Mr. Larry Wilson in the preparation and repair of research equipment is much appreciated. Mass spectra were obtained through the time and assistance of Dr. Roland Lehr, Dr. Tom Kams and Dr. A. J. Weinheimer. The assistance of Dr. Charles Hignite, Massachusetts Institute of Technology, for the first mass spectrum of the theophylline dimer is also acknowledged. Samples of 3-methylxanthine and 1,7-dimethylxanthine were supplied through the courtesy of Gertrude B. Elion, D. Sc., of Burroughs- iv Wellcome Research Laboratories, Tuckahoe, New York. Samples of 1,3- dimethyluric acid and related compounds were supplied by Hubert Goldner of Veb Arzneimittel, Dresden. The faculty, past and present departmental chairman, my ad­ visory committee and my fellow graduate students have been very generous with their assistance. Gratitude is also due the secretarial, library, maintenance and supply staff for their kindness and cordiality. The opportunity to serve on Committee S is acknowledged as a worthy educational experience. Much technical assistance, practical advice and endless moral support has been given by Dr. Tom Kams, Mr. Stephen Rehm and Dr. William Youngblood. I am very grateful for their time, assistance and concern and deeply treasure their friendship. Lastly, two communities have served as my "touchstone" through­ out these years of graduate studies. Without the sharing, caring and strength of many of my fellow Dominican Sisters of Marywood, Grand Rapids, Michigan and the body of witnessing believers centered in the Community of Thomas More, Norman, Oklahoma, these years would have been both more difficult and much less enriching. TABLE OF CONTENTS Page LIST OF TABLES.......................................... vii LIST OF ILLUSTRATIONS.................................. xi PART I. ELECTROCHEMICAL OXIDATION OF BIOLOGICALLY IMPORTANT XANTHINES INTRODUCTION..................................... 1 RESULTS AND DISCUSSION.......................... 19 EXPERIMENTAL..................................... 8 8 SUMMARY........................................... 103 REFERENCES.................................... 106 PART II. ELECTROCHEMICAL REDUCTION OF ALLOXAN, METHYL- AND DIMETHYL ALLOXAN IN AQUEOUS AND ACETONITRILE SOLUTIONS INTRODUCTION...................................... • 110 RESULTS AND DISCUSSION....................... 124 EXPERIMENTAL.................................... 208 SUMMARY........................................... 220 REFERENCES........................................ 222 vx LIST OF TABLES Table Page PART I. 1. Properties of the N-Methylated Xanthines 8 2. Diuretic Activity of the Xanthines............ 11 3. Relative Potencies of the Xanthines........... 11 4. Oxidation Potentials of N-Methylated Xanthines at Pyrolytic Graphite Electrode in 1 M HOAc... 20 5. Effects of pH on Oxidation Potential of the Xanthines at Pyrolytic Graphite Electrode 22 6 . Correlation of Peaks Observed in Uric Acid and Xanthine Cyclic Voltammograms ( 8 v sec .... 43 7. Faradaic _n Values for Electrochemical Oxidation of Caffeine..................................... 47 8 . Characteristic Properties and Identification of Caffeine Oxidation Products in 1 MHOAc.... 49 9. Concentration of Oxidation Products at Stages in Caffeine Oxidation.......................... 53 10. Determination of Caffeine Oxidation Product Concentrations.................................. 53 11. Faradaic n^ Values for Electrochemical Oxidation of Theobromine.................................. 59 12. Characteristic Properties and Identification of Theobromine Oxidation Products in 1 M HOAc. 60 13. Determination of Theobromine Oxidation Product Concentrations.................................. 62 vii Table Page PART I. 14. Faradaic n Values for Electrochemical Oxidation of Theophylline................................. 67 15. Percentage Composition Data for Solid Product. 70 16. Determination of Theophylline Oxidation Product Concentrations.................................. 81 17. Calculation of Oxidation Products per Mole of Theophylline Oxidized.......................... 82 PART II. 1. Polarographic Behavior of Dimethyl Alloxan... 125 2. Effect of Mercury Column on Size of Limiting Current for Reduction of Dimethyl Alloxan.... 130 3. Variation of Current with Temperature....... 136 4. Variation of Dissociation Constant with Temperature.................................... 137 5. Polarographic Behavior of Methyl Alloxan 142 6 . Effect of Mercury Column Height on Size of Limiting Current for Reduction of Methyl Alloxan........................................ 144 7. Comparative Current Data for Alloxan and Dimethyl Alloxan in 2 M H 2 SO4 ................. 146 8 . Coulometric Determination of the Number of Electrons Involved in Reduction of Alloxan and N-Methylated Derivatives................. 148 Vlll Table Page PART II. 9. Spectrophotometric Data for Reduction Solution of DMA at Intervals throughout a Controlled- Potential Electrolysis at -0.4 v in 1 M HOAc. 154 10. Polarographic Data for Alloxantin in pH 4.7 Acetate Buffer................................. 159 11. Polarographic Data for 0.2 Solution of Alloxan in 0.1 M TEA? in Acetonitrile........ 172 12. Effect of Mercury Column on Limiting Current for Reduction of 1.0 Alloxan in 0.1 M TEA? in Acetonitrile........................... 176 13. Diffusion Current Constants for Reduction Waves of Alloxan in 0.1 M TEAP in Acetonitrile 176 14. Data of Wawzonek and Co-Workers.............. 180 15. Current and Diffusion Current Constants for Alloxan in 0.1 M TEAP in Acetonitrile........ 180 16. Effect of Benzoic Acid Addition on Reduction Waves of Alloxan in 0.1 M TEAP in Acetonitrile 185 17. Effect of Water Addition on Reduction of Alloxan in 0.1 M TEAP in Acetonitrile........ 186 18. Determination of Faradaic n Values for Reduction of Alloxan in 0.1 M TEAP in Acetonitrile................................... 188 ix Table PART II. Page 19. Effect of TEAP on Half-Wave Potential and Current of Equal Concentration Alloxan in Acetonitrile................................... 198 LIST OF ILLUSTRATIONS Figure Page PART I. 1. Compounds Excreted by Man after Ingestion of Caffeine, Theobromine and Theophylline.... 14 2. Variation of with pH for Xanthine Oxidation...................................... 23 3. Variation of E^ with pH for 1-MethyIxanthine Oxidation...................................... 24 4. Variation of E^ with pH for 7-MethyIxanthine Oxidation....................................... 25 5. Variation of E^ with pH for 3-Methylxanthine Oxidation....................................... 26 6 . Variation of E^ with pH for 1,7-Dimethyl- P xanthine Oxidation............... 27 7. Variation of E^ with pH for 1,3-Dimethyl- xanthine (Theophylline) Oxidation............ 28 8 . Variation of E^ with pH for 3,7-Dime thy 1- xanthine (Theobromine) Oxidation............. 29 9. Variation of E^ with pH for 1,3,7-Trimethyl- xanthine (Caffeine) Oxidation................ 29 10. Variation of E^ with pH for Theophylline Oxidation (5 mv sec ^)........................ 32 11. Variation of E^ with pH for Theophylline Oxidation (20 mv sec ^)....................... 32 XI Figure Page PART I. 12. Variation of with pH for Theophylline Oxidation (200 mv sec ............... 33 13. Variation of with pH for Theophylline Oxidation (500 mv sec ............... 33 14. Voltammograms of Theophylline at Various pH Values (5
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