Journal of the Chemical Society. Perkin transactions II p. 981 - 984 (1984)
Update date:2022-08-11
Topics:
McLennan, Duncan J.
Pross, Addy
The valence-bond configuration mixing model (VBCM) is applied to the nucleophilic substitution reactions of α-carbonyl derivatives.The model appears to resolve satisfactorily a number of features of these reactions that current mechanisms have not dealt with.These include: (i) the dependence of the rate-enchancing effect of the carbonyl upon the nucleophilic strenght of the entering group, (ii) the unusually large Hammett ? value for the reaction of PhCOCH2Br with substituted pyridines, and (iii) the mechanism by which the rate-enhancing effect of the carbonyl group is transmitted to the reaction centre.
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