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Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/18835

Title: General Base Catalyzed Deprotonation of a Thiamin-derived Intermediate: Evidence for Sequential Proton Transfer in Pyridine Catalyzed Decarboxylation
Authors: Rathgeber, Steven
Advisor: Kluger, Ronald
Department: Chemistry
Keywords: Thiamin
decarboxylation
Issue Date: 15-Feb-2010
Abstract: The conjugate acid of pyridine had been found to catalyze decarboxylation of alpha-mandelylthiamin (MTh). It was proposed this occurs by association between the substrate and pyridinium ion in a pi-stacked complex prior to cleavage of the C-C bond. Despite the evidence for selective acid catalyzed decarboxylation of MTh with pyridine and its derivatives, the nature of proton transfer occuring after the C-C bond breaks and before the final products form had not been investigated. General base catalyzed deprotonation of hydroxybenzylthiamin (HBnTh) has been applied as a model for the reverse reaction of acid-catalyzed decarboxylation. Kinetic analysis of this process suggests the acceleration by a preassociated pyridinium ion and the product-determining step in the decarboxylation of MTh are facilitated by independent sequential proton transfers.
URI: http://hdl.handle.net/1807/18835
Appears in Collections:Master
Department of Chemistry - Master theses

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