Examination of Y-Deterium isotope effects for the solvolysis of model isoprenoid compounds

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Publication Type honors thesis
School or College College of Science
Department Chemistry
Creator Fan, Huijun
Title Examination of Y-Deterium isotope effects for the solvolysis of model isoprenoid compounds
Year graduated 2012
Date 2012-05
Description Model isoprenoid compounds can undergo two distinct pathways, dissociative or associative nucleophilic substitution depending on the conditions used. The dissociative pathway consists of two steps, involving a carbocation intermediate where the formation of that carbocation is rate determining. The associative pathway is concerted reaction, which does not involve carbocation formation and the rate is more governed by the strength of the attacking nucleophile. Solvolysis Reactions of the deuterium substituted model compounds are typically slower than protiated compounds when comparing the reaction rates. So the sensitive kinetic isotope effect (KIE) can be used to evaluate the dissociative or associative nature of these reactions. A kinetic isotope effect will indicate the presence of positive charge build up adjacent to CD3 (see figure 1). So kH/kD values will be measured for model associative nucleophilic substitution reactions, I would expect an associative KIE value to equal one, indicating little or no positive charge accumulation during the reaction.
Type Text
Publisher University of Utah
Subject Isopentenoids; Solvolysis; Deuterium - Isotopes
Language eng
Rights Management (c) Huijun Fan
Format Medium application/pdf
Format Extent 314,251 bytes
Permissions Reference URL https://collections.lib.utah.edu/details?id=1254588
ARK ark:/87278/s69d06pw
Setname ir_htoa
Date Created 2016-10-27
Date Modified 2019-07-10
ID 205840
Reference URL https://collections.lib.utah.edu/ark:/87278/s69d06pw