Abstract
The effect of nonspecific solvation of the relative stability of rotational isomers of 2-[2,2-dicyano-1-(methylthio)vinyl]-5-methylpyrrole was studied theoretically (HF/6-31G*) in terms of the Onsager model. In the free form this compound exists as an ensemble of four nonplanar C, N, S rotamers, the largest energy gap between which being no more than 2 kcal/mol. The effects of media whose generalized parameters correspond to chloroform and 1,2-dichlroethane reduce this gap to 0.7 and 0.5 kcal/mol. The vibration spectra of the rotamers and characteristics of the π→π* electronic transitions with intramolecular charge redistribution were calculated. Prospects of experimental studies of the solvatochromism and conformational isomerism of the title compound were discussed.
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Murzina, N.M., Vokin, A.I., Sobenina, L.N. et al. Solvatochromism of Heteroaromatic Compounds: XVI. Theoretical Study of the Effect of Nonspecific Solvation on the Rotational Isomerism and Spectral Characteristics of 2-[2,2-Dicyano-1-(methylthio)vinyl]-5-methylpyrrole. Russian Journal of General Chemistry 72, 793–798 (2002). https://doi.org/10.1023/A:1019576706388
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DOI: https://doi.org/10.1023/A:1019576706388