Hydrogen bonding between phenols and cyanides

Abstract

The association between phenols and cyanides, dissolved in carbon tetrachloride, has been measured. The shifts of the bonded OH group frequency have been determined for a range of cyanides, and correlated with the Taft inductive factors of the groups concerned. Equilibrium constants for the formation of the complexes have been determined and correlated with the frequency shifts. The influence of steric factors has been studied, and it has been found that tertiary butyl groups in the ortho positions of phenol restrict the formation of the hydrogen bond. In most cases, the C≡N group frequency is displaced to higher frequency when bonded to a phenol. This effect is unusual, and suggests that the bonding occurs through the lone pair electrons on the nitrogen atom. Some data on the widths of the association bands have been given.