The tautomerism of imidazo[4,5-e]benzo[1,2-c,3,4-c] difuroxans: A quantum chemical and experimental study

The tautomerism of imidazo[4,5-e]benzo[1,2-c,3,4-c] difuroxans: A quantum chemical and experimental study Full article

Journal

Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014

Output data

Year: 2020, Volume: 1207, Article number : 127775, Pages count : DOI: 10.1016/j.molstruc.2020.127775

Authors

Merkulova Natalia L. ¹ , Nesterov Ivan D. ¹ , Korolev Vjacheslav L. ^2,1 , Danilenko Vitaliy M. ¹ , Pivina Tatyana S. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prosp., Moscow, 119991, Russia
2	Department of Chemistry Kursk State University, 33 Radishchev str., Kursk, 305000, Russia

The tautomerism of imidazo[4,5-e]benzo[1,2-c; 3,4-c’]difuroxan in DMSO solution and in a water-acetonitrile system was studied experimentally using 1H, 13C NMR and liquid chromatography - mass spectrometry (LC-MS). The relative thermodynamic stabilities (ΔG) of 13 theoretically predicted isomeric forms of this compound and the activation barriers of their isomerization reactions (ΔGrel) in the gas phase and in DMSO medium were estimated using DFT B3LYP/6-311++G (d,p). The energy preference of some tautomeric forms with the structure of imidazo[4,5-e]benzo[1,2-c; 3,4-cʹ]difuroxan was established.

Merkulova N.L. , Nesterov I.D. , Korolev V.L. , Danilenko V.M. , Pivina T.S.
The tautomerism of imidazo[4,5-e]benzo[1,2-c,3,4-c] difuroxans: A quantum chemical and experimental study
Journal of Molecular Structure. 2020. V.1207. 127775 . DOI: 10.1016/j.molstruc.2020.127775 WOS Scopus OpenAlex

Web of science:	WOS:000517790600021
Scopus:	2-s2.0-85078464925
OpenAlex:	W3003168791

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