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Date of Award
Master of Science (M.S.)
Michael J. Minch
First Committee Member
Charles A. Matuszak
Second Committee Member
Patrick R. Jones
This study provides information about the kinetics of the hydrolytic ring cleavage of imidazolium compounds and the catalytic effect of micelles in this ring cleavage. 9-Methylcaffeine iodide was synthesized and its base catalyzed ring cleavage was studied. The ring cleavage, via alkaline hydrolysis of the imidazole moiety, showed pseudo-first order kinetics over the pH range of 7.28 to 10.81. Activation parameters were found to be: Ea = 29.4 Kcal mole-1, △H+ = 28.8 Kcal mole-1 , and △S+ = 27.4 cal mole-l deg -1 The kinetics were studied in the presence of micelles and no rate enhancement was observed. The mechanism for ring cleavage was also investigated. 9-Ethylcaffeine iodide was synthesized and its base catalyzed ring cleavage, at 30°C and a pH of 9.42, showed pseudo first order kinetics. 6 -3 -1 The kobs was found to be 1. 5 x 10-3 sec-1. The oxidation kinetics of 8 ,8-dihydro-9-methylcaffeine to 9-methylcaffeinE:· iodide were also examined.
Reimer, Karl Gregory. (1979). A kinetic study of the base catalyzed ring opening of 9-methylcaffeine halide and its homologs. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/449
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