Mechanistic study of quinone-polyalcohol interaction through cyclic voltammetry

The electrochemistry of some quinones has been focused to determine the mode of interaction in presence of polyalcohols. Three compounds of each family (benzoquinones, naphthoquinones and anthraquinones) were investigated through cyclic voltammetry in the presence of ethylene glycol (a diol)) and glycerol (a triol) in dichloromethane and acetonitrile at 25°C. The observed positive shift in both the waves of the quinone with successive addition of alcohol was attributed to hydrogen bonding in the quinone-alcohol couple. “Two electron one step” electron transfer mechanism was proposed for the increase in the first wave height at the expense of second. The depletion of the first anodic wave at higher concentration of polyalcohol was rationalized in terms of protonation-deprotonation mechanism. A prior peak observed in the presence of glycerol was ascribed to the hydrogen bonding of the alcohol with neutral quinone. The difference in basicity strength within a family as well as among the three quinone families was also addressed in view of the interaction effectiveness.