The Substituent Effect. VIII. Solvolysis of m-and p-Substituted α-Methylbenzyl Chlorides

Y Tsuno, Y Kusuyama, M Sawada, T Fujii…

Index: Tsuno,Y. et al. Bulletin of the Chemical Society of Japan, 1975 , vol. 48, # 11 p. 3337 - 3346

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Citation Number: 73

Abstract

The rates of solvolysis of twenty-two m-and p-substituted α-methylbenzyl chlorides were determined in 80% aqueous acetone. The relative rates at 45° C are not correlated linearly with σ 0 or σ. The use of Brown's σ+ improves the fit but the resulting correlation is still concave. An excellent correlation, logk⁄ k 0=− 4.950 (σ 0+ 1.147Δ\ barσ R+), was obtained by applying the LArSR equation. The r value 1.15 suggests that the π-electronic contribution ...