N-N bond cleavage in N-nitrosoarylamines

Evans, Louise A.; Petrovic, Marija; Antonijevic, Milan; Wiles, Charlotte; Watts, Paul; Wadhawan, Jay

Abstract

The rupture of N-N bonds in three specific N-nitrosoarylamines (N,N'-dimethyl-N,N-dinitroso-para-phenylenediamine, Cupferron, and N-nitrosodiphenylamine) upon electrochemical oxidation in acetonitrile solution is investigated. In two cases, viz., Cupferron and N-nitrosodiphenylamine, self-inhibition via partial blocking of the electrode due to adsorption is observed. In the case of the bis(nitroso)arylamine, waveshape analysis using the Marcus theory of steady-state voltammetry at microelectrodes suggests that the oxidation involves the formation of a dication before N-N bond cleavage or a mechanism of the ECEC type.

• Journal Article Type: Article
• Publication Date: Aug 1, 2008
• Journal: JOURNAL OF PHYSICAL CHEMISTRY C
• Print ISSN: 1932-7447
• Electronic ISSN: 1932-7455
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 112
• Issue: 33
• Pages: 12928-12935
• APA6 Citation: Evans, L. A., Petrovic, M., Antonijevic, M., Wiles, C., Watts, P., & Wadhawan, J. (2008). N-N bond cleavage in N-nitrosoarylamines. Journal of physical chemistry. C, 112(33), (12928-12935). doi:10.1021/jp710473a. ISSN 1932-7447
• DOI: https://doi.org/10.1021/jp710473a
• Keywords: General Energy; Physical and Theoretical Chemistry; Electronic, Optical and Magnetic Materials; Surfaces, Coatings and Films
• Publisher URL: https://pubs.acs.org/doi/abs/10.1021/jp710473a