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Protonation Kinetics of Anionic Intermediates in the Electrochemical Reduction of Triphenylethylene: a Disproportionation Mechanism
Farnia, Giuseppe,Maran, Flavio,Sandona, Giancarlo,Severin, Maria Gabriella
, p. 1153 - 1158 (1982)
The voltammetric behaviour of triphenylethylene (T) in dimethylformamide in the presence of traces of proton donor indicates that the radical anion (T-.) is stable, the dianion (T2-) is rapidly protonated, and the resulting carbanion (TH-) is a relatively strong base.In the presence of added water, T-. decays via disproportionation followed by protonation of T2-.This was indicated by both homogeneous and voltammetric kinetics.In fact, in homogeneous conditions, the rate of decay is second-order in -.>, enhanced by water, and inhibited by T.Voltammetric kinetics further support the proposed mechanism showing that, under particular conditions, the reaction is rate-limited by the disproportionation step.Alternative mechanisms can be disregarded on the basis of both kinetic and thermodynamic data.
