Substituent Effects on the Leaving Groups in Benzyl Arenesulfonates

Benzyl Arenesulfonate의 離脫基의 置換基效果에 關한 硏究 (第 1 報)

  • Yoh Soo Dong (Department of Chemistry, Teacher's College, Kyungpook National University)
  • 여수동 (慶北大學校 師範大學 化學科)
  • Published : 1975.04.30

Abstract

Determination has been made of the kinetics of the reaction of benzyl arenesulfonates with pyridine in acetone. The substituent effects of the leaving groups in benzyl arenesulfonates are correlated by Hammett equations, with the exception of p-MeO and $p-NO_2$ groups, where the electron attracting substituents in the benzyl arenesulfonate increase the rate. The substituent effects of the leaving groups are as expected due to the nucleophilic attack of amine on the benzyl carbon atom. This can be understood in terms of changes in bond formation (C-N) and bond breaking (C-O) in the transition state with charges in electron-attracting ability of the substituents. The predicted substituent effects may indicate a small increase in bond formation and thus a tighter transition state, in benzyl p-bromobenzene sulfonate than in benzyl p-nitrobenzenesulfonate. Predicting made by Thornton concerning the substituent effects on $S_N2$ transition state structures agrees with the changes in bond formation and bond breaking.

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