Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues

Bhabak, Krishna P and Vernekar, Amit A and Jakka, Surendar R and Roy, Gouriprasanna and Mugesh, Govindasamy (2011) Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues. In: Organic and Biomolecular Chemistry, 9 (14). pp. 5193-5200.

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Abstract

In this study, ebselen and its analogues are shown to be catalysts for the decomposition of peroxynitrite (PN). This study suggests that the PN-scavenging ability of selenenyl amides can be enhanced by a suitable substitution at the phenyl ring in ebselen. Detailed mechanistic studies on the reactivity of ebselen and its analogues towards PN reveal that these compounds react directly with PN to generate highly unstable selenoxides that undergo a rapid hydrolysis to produce the corresponding seleninic acids. The selenoxides interact with nitrite more effectively than the corresponding seleninic acids to produce nitrate with the regeneration of the selenenyl amides. Therefore, the amount of nitrate formed in the reactions mainly depends on the stability of the selenoxides. Interestingly, substitution of an oxazoline moiety on the phenyl ring stabilizes the selenoxide, and therefore, enhances the isomerization of PN to nitrate.

Item Type:	Journal Article
Publication:	Organic and Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	18 Jul 2011 08:31
Last Modified:	18 Jul 2011 08:31
URI:	http://eprints.iisc.ac.in/id/eprint/39087

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