Linear Solvation Energy Relationship in the Reaction between Phenacyl Bromide and 2-Mercaptobenzothiazole

Abstract

The reaction between phenacyl bromide and 2-mercaptobenzothiazole was studied conductometrically in 17 different protic and aprotic solvents. The second order rate constants determined are found to be highly susceptible to changes in the solvation abilities of the solvents. Correlation of the rate constants with different solvent parameters indicated that the solvation of the reactants and the transition state is due to the electrophilicity, hydrogen bond donor ability, specific polarisability and a non-specific polarity of the solvent. by statistical analysis, a linear solvation energy relationship is derived and the percentage contributions of each type of solvation are estimated.