Carbanion intermediates in the electro-reduction of polycyclic aromatic hydrocarbons

Abstract

The carbanions formed by monoprotonation of the dianions of some polycyclic aromatic hydrocarbons in formally aprotic solvents can be detected by rapid sweep cyclic voltammetry at a platinum electrode. Those derived from alternant hydrocarbons are oxidized at essentially one potential. Those derived from non-alternant hydrocarbons are oxidized less readily, and at differing potentials. Gas-phase ionization potentials of the anions and electron affinities of the corresponding cations are derived from the solution data.