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


Chan, B and O'Reilly, RJ and Easton, CJ and Radom, L, Reactivities of amino acid derivatives toward hydrogen abstraction by Cl and OH, The Journal of Organic Chemistry (Washington), 77, (21) pp. 9807-9812. ISSN 0022-3263 (2012) [Refereed Article]

Copyright Statement

Copyright 2012 American Chemical Society

DOI: doi:10.1021/jo3021538


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-CH. 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.

Item Details

Item Type:Refereed Article
Keywords:amino acid, reacticity, hydrogen abstraction
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Free radical chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:O'Reilly, RJ (Dr Robert O'Reilly)
ID Code:118245
Year Published:2012
Web of Science® Times Cited:43
Deposited By:Chemistry
Deposited On:2017-07-07
Last Modified:2017-08-21

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