Synthesis and spin-trapping properties of a new spirolactonyl nitrone

Yongbin Han, Beatrice Tuccio, Robert Lauricella, Antal Rockenbauer, Jay L. Zweier, Frederick A. Villamena

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Abstract

(Chemical Equation Presented) Spin trapping using electron paramagnetic resonance (EPR) spectroscopy is commonly employed for the identification of transient radicals in chemical and biological systems. A spirolactonyl-nitrone with rigid H-bond acceptor, 7-oxa-1-azaspiro[4.4]non-1-en-6-one 1-oxide, CPCOMPO, has been synthesized and characterized, and its spin-trapping properties were investigated. The rate of formation of CPCOMPO-O2H was determined using competition kinetics between the superoxide/hydroperoxyl radical (O2•-/HO2) trapping by CPCOMPO and the spontaneous dismutation of this radical in aqueous media. The rate constant of 60 M-1·s-1 is the highest rate constant thus far observed at neutral pH for any nitrones using the kinetic method employed. Decay kinetics were also experimentally investigated for CPCOMPO-O2H. The effect of rigid H-bond acceptor on the stability of the CPCOMPO-O2H were computationally rationalized and compared to that of EMPO-O2H, which has flexible H-bond acceptor, and results show the need of a "loose" H-bond acceptor for improved adduct stability.

Original languageEnglish
Pages (from-to)2533-2541
Number of pages9
JournalJournal of Organic Chemistry
Volume73
Issue number7
DOIs
Publication statusPublished - Apr 4 2008

ASJC Scopus subject areas

  • Organic Chemistry

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    Han, Y., Tuccio, B., Lauricella, R., Rockenbauer, A., Zweier, J. L., & Villamena, F. A. (2008). Synthesis and spin-trapping properties of a new spirolactonyl nitrone. Journal of Organic Chemistry, 73(7), 2533-2541. https://doi.org/10.1021/jo702434u