Electrochemical oxidation of 6-propionyl-2-(N,N-dimethylamino)naphthalene (prodan) in acetonitrile on Pt electrodes: Reversible dimerization of prodan radical cations

The electrooxidation of 6-propionyl-2-(N,N-dimethylamino)naphthalene (prodan) has been investigated for the first time. It has been performed on both conventional size platinum electrodes and platinum ultramicroelectrodes in acetonitrile by cyclic voltammetry with convolution analysis and controlled-potential electrolysis. The voltammetric responses at room temperature are similar to those corresponding to a kinetically controlled anodic electron-transfer process. Cyclic voltammetry measurements were also carried out at different concentrations of prodan and at different temperatures. Chemical transformation of the radical monocation formed after the electrochemical oxidation of prodan, as deduced from reverse controlled potential bulk electrolysis and cyclic voltammetry measurements, gives evidence for the reversible dimerization of prodan radical cations. Both diagnostic criteria and digital simulation confirm that radical–radical coupling is the reversible chemical reaction coupled to the initial elect...

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