Dissociation of phenols and phenolate salts and homocomplexation in the corresponding phenol–phenolate systems in benzonitrile

Abstract

The acidities of 12 substituted phenols (pK^BN_a relative to the pK^BN_a of HClO₄) and the formation constants of the corresponding homocomplexes, K_AHA, in benzonitrile have been determined from e.m.f. measurements. Comparison with previous results reveals that the stability of homocomplexes increases in aprotic solvents in the order acetonitrile ≈ propylene carbonate < benzonitrile < acetone. Conductivity measurements have been carried out on the 12 tetrabutylammonium phenolates in benzonitrile. The data have been analysed using the Pitts equation and the limiting conductivities and dissociation constants of the salts have been calculated.