Journal of physical organic chemistry

Solvolysis of benzylic chlorides with extended charge delocalization. α??tert??butyl (2??naphthyl) methyl, 9??fluorenyl and monosubstituted benzhydryl chlorides

KT Liu, YS Lin, ML Tsao

Index: Liu, Kwang-Ting; Lin, Yen-Shyi; Tsao, Meng-Lin Journal of Physical Organic Chemistry, 1998 , vol. 11, # 3 p. 223 - 229

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Citation Number: 27

Abstract

Abstract Rate constants of solvolysis of α-tert-butyl (2-naphthyl) methyl chloride (1), 9- fluorenyl chloride (2) and a series of monosubstituted benzhydryl chlorides (3) in a wide range of solvents were measured. Grunwald–Winstein-type correlation analysis of log k for 2 and 3 against Y BnCl, with or without nucleophilicity N, yielded less satisfactory linear correlations than that against log k (1). A new scale of solvent ionizing power, Y xBnCl, for ...