Mechanism of Thiol-Induced Nitrogen(II) Oxide Donation by Furoxans: a Quantum-Chemical Study

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 n...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-11, Vol.51 (11-12), p.951-960
Main Authors: Burov, Oleg N., Kletskii, Mikhail E., Fedik, Nikita S., Lisovin, Anton V., Kurbatov, Sergey V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Donations
Nitric oxide
Organic Chemistry
Pharmacy
Thiols
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-016-1804-z