Alkyl radical adducts of aromatic N-oxides as hydrogen-abstracting agents: The reactivity of phenazine-N,N′-dioxide-methyl radical adduct

Alkyl radical adducts of aromatic N-oxides as hydrogen-abstracting agents: The reactivity of... An O-methylated analog of protonated phenazine-di-N-oxide radical anion abstracts hydrogen from primary and secondary alcohols in a slow (k 1 < 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Alkyl radical adducts of aromatic N-oxides as hydrogen-abstracting agents: The reactivity of phenazine-N,N′-dioxide-methyl radical adduct

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Publisher
Springer Journals
Copyright
Copyright © 2006 by VSP
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856706778400325
Publisher site
See Article on Publisher Site

Abstract

An O-methylated analog of protonated phenazine-di-N-oxide radical anion abstracts hydrogen from primary and secondary alcohols in a slow (k 1 < 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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jan 1, 2006

References

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