Effects of hydrogen bonding and homoconjugation on the titration curves of a synthetic polynuclear phenolic compound in non-aqueous solvents

Abstract

A straight chain polynuclear phenolic compound containing 9 phenolic nuclei has been synthesized and titrated in several non-aqueous solvents. In some of the solvents, a stepwise neutralization of OH groups in the compound has been observed. Some of the OH groups in the compound have a hyperacid character, and a sharp increase in conductance was observed as these OH groups are neutralized by the base. Some of these features have been discussed in terms of intramolecular hydrogen bonding and homoconjugation between the acid and its anion.