title: Re-examination of the anodic oxidation of N,N-dimethylaniline, using parametric method 3.
abstract: A semi-empirical calculation (PM3) was applied to elucidate the anodic oxidation mechanism of N,N-dimethylaniline (DMA) and the dimerization of a cation radical (A) derived from DMA was ruled out. The heat of reaction value of the dimerization of A was 42.43 kcal/mol. We propose the following. Cation radical A reacts with DMA to generate another cation radical (D). This reaction was exothermic and the heat of reaction value and the activation energy were -0.35 kcal/mol and 1.31 kcal/mol, respectively. Deprotonation of D by DMA gives neutral radical (E), which is oxidized to TMB by A. All these reactions were exothermic.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kobe-Gakuin University, Japan. michida@pharm.kobegakuin.ac.jp
authors.forename: T
authors.initials: T
authors.lastname: Michida
authors.forename: E
authors.initials: E
authors.lastname: Osawa
authors.forename: Y
authors.initials: Y
authors.lastname: Yamaoka
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003500:Cyclization; D004566:Electrodes; D005609:Free Radicals; D010084:Oxidation-Reduction
chemical_list: D000814:Aniline Compounds; D005609:Free Radicals; C015157:N,N-dimethylaniline