TY - JOUR
T1 - Reactivities of amino acid derivatives toward hydrogen abstraction by Cl· and OH·
AU - Chan, Bun
AU - O'Reilly, Robert J.
AU - Easton, Christopher J.
AU - Radom, Leo
PY - 2012/11/2
Y1 - 2012/11/2
N2 - 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.
AB - 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.
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U2 - 10.1021/jo3021538
DO - 10.1021/jo3021538
M3 - Article
C2 - 23061734
AN - SCOPUS:84868372241
VL - 77
SP - 9807
EP - 9812
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 21
ER -