Title
Alkyl Radical Adducts of Aromatic N-Oxides as Hydrogen-Abstracting Agents: The Reactivity of Phenazine-N,N′-Dioxide-Methyl Radical Adduct
Document Type
Article
Publication Date
10-23-2006
Description
An O-methylated analog of protonated phenazine-di-N-oxide radical anion abstracts hydrogen from primary and secondary alcohols in a slow (k1 < 500 M-1 s-1) bimolecular reaction. No kinetic evidence has been found for the unimolecular release of free methoxyl radicals through the homolytic N-OMe bond cleavage in these species. DFT calculations at the UB3LYP 6-31G(d) level indicate that protonated and O-alkylated radical anions of pyrazine, quinoxaline and phenazine di-N-oxides are close analogues of aromatic nitroxyl radicals with the highest spin density localized on the oxygen and nitrogen of the nitrone moiety.
Citation Information
Razskazovskiy, Yuriy; and Close, David M.. 2006. Alkyl Radical Adducts of Aromatic N-Oxides as Hydrogen-Abstracting Agents: The Reactivity of Phenazine-N,N′-Dioxide-Methyl Radical Adduct. Research on Chemical Intermediates. Vol.32(7). 625-635. https://doi.org/10.1163/156856706778400325 ISSN: 0922-6168