Hydrogen-Bonding and Protonation Effects in Electrochemistry of Quinones in Aprotic Solvents

摘要

Hydrogen-bonding and protonation are fundamental factors controlling potentials and mechanisms in the reduction of quinines. These are studied systematically in benzonitrile, acetonitrile, and dimethylsulfoxide solutions by cyclic voltammetry of a series of quinines of increasing basicity (chloranil to duroquinone), in the presence of hydroxylic additives of increasing hydrogen-bonding power (tert-butyl alcohol to hezafuloro-2-propanol) or acidity (trifluoroacetic acid).