Abstract
Abstract Trico-ordinate phosphorus compounds, ArηP(OPri)3-η where n = 0–3, react with tetracyanoquino-dimethane (TCNQ) in acetonitrile in the presence of water to give the corresponding phosphoryl compounds, ArηP(O)(OPri)3-η and 1,4-bis-dicyanomethylbenzene (TCNQH2) in quantitative yield. The kinetics of these reactions are reported together with the Hammett ρ-parameters from variation of substituents in the aryl group for n = 1,2 and 3. On the basis of the available evidence, a mechanism is proposed involving one electron transfer from phosphorus (the donor) to TCNQ. A kinetic study of the reaction of triarylphosphines with TCNE in aqueous acetonitrile, however, suggests rate-limiting nucleophilic attack on nitrogen rather than the radical cation mechanism.
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