Cyclization of 4-Hydroxy-4-methyl-1-pentyl p-Toluenesulfonate as a Model to Evaluate Inherent Medium Effect on SN2 Solvolysis

Abstract Solvent effect on the cyclization of 4-hydroxy-4-methyl-1-pentyl p-toluenesulfonate, a mechanistic equivalent to the SN2 solvolysis, was successfully analyzed by the Taft LSER equation as log k = 3.2π* + 1.4α + 1.9β − 8.36, indicating that three independent factors are operative, i.e., solvent polarity and H-bond donor ability which promote ionization, and H-bond acceptor ability which enhances nucleophilicity of the internal OH group.