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http://dx.doi.org/10.5012/jkcs.2019.63.4.233

Mechanistic Studies of the Solvolyses of Cyclohexanesulfonyl Chloride  

Kang, Suk Jin (Department of Science Education, Jeonju National University of Education)
Koh, Han Joong (Department of Science Education, Jeonju National University of Education)
Publication Information
Journal of the Korean Chemical Society / v.63, no.4, 2019 , pp. 233-236 More about this Journal
Abstract
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 $S_N2$ mechanism in which bond formation is more important than bond breaking in the transition state (TS). Relatively small activation enthalpy values (11.6 to $14.8kcal{\cdot}mol^{-1}$), the large negative activation entropy values (-29.7 to $-38.7cal{\cdot}mol^{-1}{\cdot}K^{-1}$) and the solvent kinetic isotope effects (SKIE, 2.29, 2.30), the solvolyses of the cyclohexanesulfonyl chloride (1) proceeds via the $S_N2$ mechanism.
Keywords
Cyclohexanesulfonyl chloride; Extended Grunwald-Winstein equation; $S_N2$ mechanism; Solvent kinetic isotope effect;
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