Nucleophilic displacement at the benzoyl centre: a study of the change in geometry at the carbonyl carbon atom

MJ Colthurst, A Williams

Index: Colthurst, Matthew J.; Williams, Andrew Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 8 p. 1493 - 1497

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Abstract

The second-order rate constants for the reaction between hydroxide ion and phenoxide ion with 4-nitrophenyl esters of substituted benzoic acids in 10% acetonitrile–water (v/v) solution obey Hammett σ correlations. The values of the Hammett ρ of 1.67 (kArO) and 2.14 (kOH) are consistent with a large change in hybridization at the central carbon by comparison with the ρ value for a standard reaction where a full sp2 to sp3 change occurs. The transition ...

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