Protonation Kinetics of Anionic Intermediates in the Electrochemical Reduction of Triphenylethylene: a Disproportionation Mechanism

DOI: 10.1039/P29820001153

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1153 - 1158 (1982)

Update date:2022-07-30

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Authors:

Farnia, Giuseppe

Maran, Flavio

Sandona, Giancarlo

Severin, Maria Gabriella

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Article abstract of DOI:10.1039/P29820001153

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 (T^2-) 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 T^2-.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.

Full text of DOI:10.1039/P29820001153

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