Solvent effect on the reaction of tosyl chloride with p-substituted phenol(s) and triethylamine

Second-order rate constants have been determined conductometrically for the nucleophilic substitution reactions of tosyl chloride with p-substituted phenol(s) and triethylamine in different solvents system. Studies on solvent effects on the reactions by applying correlation techniques(simple and multiple regression) have been done. The rate of the reaction depends on the degree of charge separation on the p-substituted phenol(s)-triethylamine complex, which is influenced by the solvent properties. We have classified the solvents into three sets (A,B and C) to make the study more meaningful. The set A consists of mainly aliphatic polar aprotic solvents, set B consists of aromatic and halogenated solvents and set C consists of protic hydroxylic solvents. Solvent parameters at macroscopic and microscopic level were used. The coefficient of the solvent parameters provide a good information to predict and to analyse the reaction mechanism.

Author(s): Nagarajan Vembu1 and Chandrasekaran Arunmozhithevan2

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