Abstract
The electrochemical oxidation of N, N-dimethyl-1-naphthylamine (DMN) has been studied at the platinum electrode in acetonitrile by cyclic voltammetry, controlled potential electrolysis and spectroscopic methods. In neutral medium a complex ECE type of mechanism is inferred. The action radical produced in the first charge transfer step dimerizes by C 4- C′ 4 coupling giving N,N,N′,N′-tetramethyl-1-naphthidine (TMN) which oxidizes further to dication (TMN 2+). The mechanism of reaction is discussed. The studies in acid medium confirm the proposals. An interesting feature was observed in the studies with addition of bases: pyridine (Py) and 2,6-lutidine. The cyclic voltammograms in the presence of these bases show an unusual curve crossing. This curve crossing diminishes with scan rate and increases with Py concentration. Several evidences allowed us to propose that this effect is due to an homogeneous redox reaction between TMN 2+ and DMN coupled to the previously described ECE mechanism.
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