Reactivities of amino acid derivatives toward hydrogen abstraction by Cl· and OH·

Bun Chan, Robert J. O'Reilly, Christopher J. Easton, Leo Radom

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

In recent computational studies of hydrogen-atom abstraction from amino acid derivatives, two distinct rationalizations have been put forward for the relative inertness of the α-C-H. Of these, the proposal that the inertness is due to a "kinetic trap" associated with particularly stable complexes is shown to be unlikely because of unfavorable entropies. On the other hand, the proposed existence of deactivating polar effects at the α-position in Cl· abstractions is likely also to be applicable to OH· abstractions, but to a lesser extent.

Original languageEnglish
Pages (from-to)9807-9812
Number of pages6
JournalJournal of Organic Chemistry
Volume77
Issue number21
DOIs
Publication statusPublished - Nov 2 2012

ASJC Scopus subject areas

  • Organic Chemistry

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