Tetrahedron

Solvent influences on initial and transition states in solvolysis of 2-chloroethyl methyl sulfide

MR Sedaghat-Herati, JM Harris, SP McManus

Index: Sedaghat-Herati, M. R.; Harris, J. M.; McManus, S. P. Tetrahedron, 1988 , vol. 44, # 24 p. 7479 - 7488

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Abstract

Nucleophilic substitution reactions of 2-(alkylthio) ethyl derivatives have become important in understanding basic principles of physical organic chemistry. In the present work the solvent effects of 2-chloroethyl methyl sulfide (1-Cl) solvolysis in methanol, methanol-water mixtures, and water are analyzed to provide a dissection of initial-state (IS) and transition- state (TS) effects. The reduction in activation energy accompanying replacement of ...