Electrochemical reduction of aromatic thiocarbonyls to the corresponding radical anions

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Abstract
Evidence for the presence of radical anions from electrochemical reduction of aromatic thiocarbonyl derivatives has been obtained by means of e.s.r. spectroscopy. A linear dependence between the electromotive force for reducing such a class of compound and that for the corresponding carbonyl derivatives has been observed. Computer-simulated spectral analyses allowed the determination of the proton hyperfine splitting constants. The aN value for the nitrogen splitting in the 4,4′-dinitro-substituted derivative could be estimated by using a deuterio-substituted compound. Sets of Coulomb and resonance integrals for double-bonded sulphur have been discussed and a pair of values suggested for the calculation of the spin density distribution. The latter values lead to a qualitative agreement between the energy values of the lowest antibonding orbitals and the experimental reduction potentials.

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