Polarographic and spectroscopic study of some quinones and their hydroxyl-substituted derivatives

Abstract

The effect of intramolecular hydrogen-bonding on the π-electron energy levels of hydroxyquinones has been investigated polarographically and spectroscopically. The results have been compared with energies calculated by the Hückel molecular orbital method; the parameters which have been suggested for this type of problem do not give a satisfactory interpretation of the experimental observations. This may be due to the transfer of the hydrogen bonding proton across the hydrogen bond during electron addition.