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Outcome-changing effect of polarity reversal in hydrogen-atom-abstraction reactions

Chan, Bun; Easton, Christopher; Radom, Leo


We have examined hydrogen-atom-abstraction reactions for combinations of electrophilic/nucleophilic radicals with electrophilic/nucleophilic substrates. We find that reaction between an electrophilic radical and a nucleophilic substrate is relatively favorable, and vice versa, but the reactions between a radical and a substrate that are both electrophilic or both nucleophilic are relatively unfavorable, consistent with the literature reports of Roberts. As a result, the regioselectivity for the...[Show more]

CollectionsANU Research Publications
Date published: 2015
Type: Journal article
Source: Journal of Physical Chemistry A
DOI: 10.1021/acs.jpca.5b01890


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