Formation reactions of phosphorus ylide–tetracyanoquinodimethane complexes

Abstract

The complexation reactions of tetracyanoquinodimethane (TCNQ) with phosphorus ylides have been studied. The binding energy is related to the electron density on the ylide atom as controlled by substituents. The degree of charge-transfer in the complex is also controlled by the substituents. The rate of formation of ylide–TCNQ complexes is slow enough to be measured, and a correlation between the reaction rate and the basicity of the ylide atoms was also established.