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Mechanistic Studies of the Solvolyses of Cyclohexanesulfonyl Chloride

Kang, Suk Jin;Koh, Han Joong

  • Received : 2019.03.15
  • Accepted : 2019.04.03
  • Published : 2019.08.20

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