Reaction of Leucocrystal Violet with Tetracyanoethylene and Chloranil II. Solvent Effects

Abstract

The proton/deuteron transfer reaction of Leucocrystal Violet(LCV) with tetracyanoethylene(TCNE) and chloranil(CA) in various solvents has been followed spectrophotometrically. It was found that the reaction proceeds slower in polar solvents such as acetonitrile and acetone than in less polar solvents such as chloroform and 1,2-dichloroethane. The rate is remarkably accelerated by pressure indicating probably a substantial polarity increase in the rate processes. The formation of CT complexes was observed at low temperatures. Their nature is presumed to be similar to that of a complex formed by the reaction of CA with N,N-dimethyl-p-toluidine(DMT), and the latter is discussed in connection with the reaction rate of the LCV–TCNE and LCV–CA systems. A possible reaction path is proposed.