Journal of the American Chemical Society

Group transfers. 1. Enolate structures contributing to the transition state for nucleophilic substitution on. alpha.-substituted carbonyl compounds

TI Yousaf, ES Lewis

Index: Yousaf, T. I.; Lewis, E. S. Journal of the American Chemical Society, 1987 , vol. 109, # 20 p. 6137 - 6142

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Citation Number: 30

Abstract

Abstract: The high SN2 reactivity of a-halocarbonyl compounds is explained by the lowering of the intrinsic barrier by a major contribution of enolate structure to the transition state. This theoretical conclusion is now shown experimentally. The evidence is as follows:(1) Change in structure of a leaving arenesulfonate ion does not change the rates of attack of benzenesulfonate ion by nearly as much as it changes the equilibrium constants. A ...

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