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Alkyl Radical Adducts of Aromatic N-Oxides as Hydrogen-Abstracting Agents: The Reactivity of Phenazine-N,N′-Dioxide-Methyl Radical Adduct

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.

Identiferoai:union.ndltd.org:ETSU/oai:dc.etsu.edu:etsu-works-19474
Date23 October 2006
CreatorsRazskazovskiy, Yuriy, Close, David M.
PublisherDigital Commons @ East Tennessee State University
Source SetsEast Tennessee State University
Detected LanguageEnglish
Typetext
SourceETSU Faculty Works

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