Transition state imbalance in the deprotonation of substituted 2-tetralones by hydroxide ion

JB Nevy, DC Hawkinson, G Blotny, X Yao…

Index: Nevy, John B.; Hawkinson, David C.; Blotny, Grzegorz; Yao, Xudong; Pollack, Ralph M. Journal of the American Chemical Society, 1997 , vol. 119, # 52 p. 12722 - 12726

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Citation Number: 25

Abstract

Rate and equilibrium constants for the deprotonation of a series of phenyl-substituted 2- tetralones in aqueous sodium hydroxide have been determined. A Brønsted plot of log k for deprotonation vs p K a of the appropriate 2-tetralone is linear with a slope (-α) of-0.60±0.01, except for the point corresponding to 6-nitro-2-tetralone (1b). The negative deviation of 1b from the correlation indicates that the transition state for deprotonation of 2-tetralone is ...