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MECHANISM OF THIOL-INDUCED NITROGEN(II) OXIDE DONATION BY FUROXANS: A QUANTUM-CHEMICAL STUDY

Олег Н. Буров, Михаил Е. Клецкий, Никита С. Федик, Антон В. Лисовин, Сергей В. Курбатов
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Abstract


Quantum-chemical calculations according to DFT with UB3LYP functional in the 6-311++G** basis set, and accounting for solvation effects by the polarized continuum method were used to study the mechanisms of thiol-induced fragmentation of unsubstituted and annulated furoxans with the elimination of nitrogen(II) oxide. A preference for NO formation according to the radical mechanism involving an attack by sulfanyl radical (HS˙) on the carbon atom bonded to the N-oxide group was demonstrated for all systems. Anionic mechanisms involving HS anions were not feasible in any of the cases due to high endothermic effects.

How to Cite
Burov, O. N.; Kletskii, M. E.; Fedik, N. S.; Lisovin, A. V.; Kurbatov, S. V. Chem. Heterocycl. Compd. 2015, 51, 951. [Khim. Geterotsikl. Soedin. 2015, 51, 951.]

For this article in the English edition see DOI 10.1007/s10593-016-1804-z

 


Keywords


furoxans; nitrogen(II) oxide; DFT calculations; thiol-induced NO donation mechanism

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