Anodic oxidation of aromatic aza hydrocarbons

Autor: Lynn Marcoux, Ralph N. Adams
Rok vydání: 1974
Předmět:
Zdroj: Journal of Electroanalytical Chemistry and Interfacial Electrochemistry. 49:111-122
ISSN: 0022-0728
DOI: 10.1016/s0022-0728(74)80351-7
Popis: Summary The anodic oxidation of several mono- and di-azaaromatic hydrocarbons in acetonitrile has been studied by a variety of electroanalytical techniques. With the exception of pyridine all of the compounds studied were found to be oxidized in a chemically complicated process. The overall reaction was found to require one electron per mole, and in the case of acridine the electrolysis product was found to be acridylacridinium perchlorate. The results of potential dependent chronocoulometric measurements carried out upon acridine were compared with those predicted by digital simulation for the several alternative mechanisms. The results indicated that the reaction pathway most likely was AcH − e − ⇄ AcH + AcH + + AcH → k ( AcH ) 2 + k = 1.3 × 10 5 1 mol − 1 s − 1 ( AcH ) 2 + − e − ⇄ ( AcHAc ) + + H + AcH + + ( AcH ) 2 + ⇄ ( AcHAc ) + + AcH + H + This general mechanism should be operative wherever the compound being oxidized is appreciably nucleophilic, and the diagnostic technique employed should be generally useful under these conditions.
Databáze: OpenAIRE