Acetolysis reactivities of substituted benzyl and polycyclic arylmethyl p-toluenesulfonates. Correlations with SCF [self-consistant field]-. pi. and CNDO [complete …

A Streitwieser Jr, HA Hammond…

Index: Streitwieser,A. et al. Journal of the American Chemical Society, 1970 , vol. 92, # 17 p. 5141 - 5150

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Citation Number: 57

Abstract

Abstract: Acetolysis kinetics were determined for several substituted benzyl tosylates. Relative rates at 40'are p-CH3, 56.3; m-CH3, 2.66; pF, 2.45; H, 1.00; p-C1, 0.504; m-C1, 0.0510; m-CF3, 0.0261; p-CFs, 0.0162. Comparison with Brown and Okamoto's a+ values gives a division into two lines, one for activating substituents giving p=-5.71= t 0.09, and one for deactivating substituents having p=-2.33= t 0.04. Similar kinetic studies are described ...