Mechanistic Studies of the Solvolyses of Cyclohexanesulfonyl Chloride

Journal of the Korean Chemical Society

article

Suk Jin Kang¹  Han Joong Koh¹ 

[1] Department of Science Education, Jeonju National University of Education

关键词: Cyclohexanesulfonyl chloride;    Extended Grunwald-Winstein equation;    SN2 mechanism;    Solvent kinetic isotope effect;   

DOI  :  10.5012/jkcs.2019.63.4.233

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

In this study, the solvolysis of cyclohexanesulfonyl chloride (1) was studied by kinetics in ethanol-water, methanol-water, acetone-water, and 2,2,2-trifluoroethanol (TFE)-water binary solvent systems. The rate constants were applied to the extended Grunwald-Winstein equation, to obtain the values of m = 0.41 and l = 0.81. These values suggested SN2 mechanism in which bond formation is more important than bond breaking in the transition state (TS). Relatively small activation enthalpy values (11.6 to 14.8 kcal·mol-1), the large negative activation entropy values (-29.7 to -38.7 cal·mol-1·K-1) and the solvent kinetic isotope effects (SKIE, 2.29, 2.30), the solvolyses of the cyclohexanesulfonyl chloride (1) proceeds via the SN2 mechanism.

【 授权许可】

Unknown