Abstract
Rapid scan cyclic voltammetry was used to investigate the mechanism of the anodic oxidation and dimerization of N, N-dimethylaniline (DMA) in acetonitrile solution. The reduction wave for the DMA .+ radical cation was observed at scan rates above 500 V s −1. Electrogenerated DMA .+ radical cations underwent a second-order radical cation-radical cation coupling with deprotonation to form N, N, N′, N′-tetramethylbenzidine; no evidence of polymerization was detected. The experimental results best fit an EC 2EE reaction mechanism determined by fitting the data with working curves obtained by digital simulation. A rate constant of 6.3 × 10 5 M −1 s −1 was found for the coupling reaction. The clean reaction process suggests that the oxidation of DMA can serve as a model for the EC 2EE reaction mechanism in kinetic studies.
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