Abstract

The nucleophilic substitution reactions of a series of O-ethyl S-aryl dithiocarbonates with a series of secondary alicyclic amines have been investigated, all in water-ethanol mixtures and some of them in protic and dipolar aprotic solvents. The solvent effects on rate and mechanism are studied using a multiparametric approach with solvent parameters such as acidity, basicity and polarity/polarizability. These results show that in a concerted mechanism, rate constants are increased by the increase of the solvent dipolarity/polarizability. © 2012 John Wiley & Sons, Ltd.