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.
","abstract_html":"<p>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<sup>-1</sup>, △H<sup>+</sup> = 28.8 Kcal mole<sup>-1</sup> , and △S<sup>+</sup> = 27.4 cal mole<sup>-l</sup> deg <sup>-1</sup> 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 k<sub>obs</sub> was found to be 1. 5 x 10<sup>-3</sup> sec<sup>-1</sup>. The oxidation kinetics of 8 ,8-dihydro-9-methylcaffeine to 9-methylcaffeinE:· iodide were also examined.</p>","abstract_has_math":false,"creators":["Reimer, Karl Gregory"],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis","degree_discipline":"Graduate School","degree_department":null,"school":null,"contributors":["Michael J. Minch"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1979,"date_issued":"1979-01-01T08:00:00Z","date_published":"1979-01-01T08:00:00Z","updated_at":"2026-07-24T05:36:21Z","subjects":["Halides","Micelles","Methylation","Physical Sciences and Mathematics"],"languages":[],"rights":[],"rights_urls":["http://rightsstatements.org/vocab/NKC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://scholarlycommons.pacific.edu/uop_etds/449","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Michael J. Minch"]},{"key":"dc:creator","label":"Author","values":["Reimer, Karl Gregory"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["1979-01-01T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Graduate School"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Halides","Micelles","Methylation","Physical Sciences and Mathematics"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["http://rightsstatements.org/vocab/NKC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholarlycommons.pacific.edu/uop_etds/449"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:source","label":"Dc Source","values":["95"]},{"key":"dc:title","label":"Title","values":["A kinetic study of the base catalyzed ring opening of 9-methylcaffeine halide and its homologs"]}]}],"canonical_facts":{"dc:contributor":["Michael J. Minch"],"dc:creator":["Reimer, Karl Gregory"],"dc:date.available":["1979-01-01T08:00:00Z"],"dc:description.abstract":["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.
"],"dc:identifier":["https://scholarlycommons.pacific.edu/uop_etds/449"],"dc:rights":["http://rightsstatements.org/vocab/NKC/1.0/"],"dc:source":["95"],"dc:subject":["Halides","Micelles","Methylation","Physical Sciences and Mathematics"],"dc:title":["A kinetic study of the base catalyzed ring opening of 9-methylcaffeine halide and its homologs"],"thesis:degree_discipline":["Graduate School"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T05:36:21Z"}