Abstract
Summary The electrochemical reduction of several halonitrobenzenes has been studied in dimethylformamide (DMF), acetonitrile (AN), and dimethyl sulfoxide (DMSO). The initial reduction is a one-electron process which yields the corresponding anion radical. Dissociation of the anion radicals to give a neutral nitrophenyl radical and halide ion occurs quite rapidly for o-bromonitrobenzene and the three isomers of iodonitrobenzene. Nitrobenzene is then formed as a result of an abstraction of a hydrogen atom from either the solvent or the supporting electrolyte by the nitrophenyl radical. The stability of the anion radicals in the three solvent systems decreases in the order: DMSO > AN > DMF. The order of the rates of the decomposition of the anion radicals is the same in all three solvents: o-iodo-> o-bromo- ≫ p-iodo- > m-iodonitrobenzene. The addition of iodide ion significantly decreases the decomposition rates of all iodonitrobenzene anion radicals. The addition of bromide ion has little or no effect on either the stability of the anion radical of o-bromonitrobenzene or the anion radicals of the iodonitrobenzenes.
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