Add time:08/04/2019         Source:sciencedirect.com

The homogeneous and electrode electron transfer to triphenylmethyl phenyl sulphide was analyzed as a function of the reaction Gibbs energy. Several electrogenerated aromatic anion radicals, characterized by increasing standard potentials, were used as homogeneous electron transfer reagents. This reaction was studied either by the method of homogeneous redox catalysis or by the usual techniques of homogeneous kinetics, according to the reaction time scale. Voltammetric measurements gave information on the heterogeneous reaction also. The product yields in the macroscale reduction showed that a C-S bond cleavage is induced by the electron transfer, giving rise quantitatively, in both cases, to an overall dissociative process. The experimental data for the homogeneous reaction seem to indicate a transition between a sequential electron transfer-bond breaking path and a direct concerted one, upon variation of the reaction driving force. Rather crude approximations of the dependence of the Gibbs energy surfaces on reaction coordinates allowed a rough estimation of the activation parameters for the anion radical formation and fragmentation. A tentative interpretation of the difference with the corresponding values previously found for the mono- and diphenylmethyl derivatives is given in terms of the effect of the three phenyl rings on either the initial or the product states.

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