Electrochemical behaviour of chlorobenzenesulphonamide derivatives at the mercury electrode in non-aqueous solvents

Abstract

The analysis of polarographic and coulometric results shows that the overall reduction mechanism of chlorobenzenesulphonamide derivatives occurs with the cleavage of the CCl bond followed by the reduction of the benzenesulphonamide involving the SN bond breaking. However, the E sol1 2 values fit the structural relation E 1 2 - E LUMO for the series of benzenesulphonamides and not that of the cholorobenzene derivatives and the shape of the LUMO of cholorobenzenesulphonamides is similar to that of the benzenesulphonamide, so that it is sensible to suggest that the first step of the reduction mechanism is the same for all the benzenesulphonamide derivatives and involves the CSN moiety of the molecules.