I. Sterkhova, M. Y. Moskalik, B. Shainyan
Apr 23, 2014
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Influential Citations
12
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Journal
Russian Journal of Organic Chemistry
Abstract
The structure of trifluoro-N-(3-formylcyclohept-2-en-1-yl)methanesulfonamide and its self-association in solution have been studied by IR spectroscopy and quantum chemical methods [B3LYP/6-311G(d,p), AIM]; proton affinities of basic centers in its molecule have been evaluated. Trifluoro-N-(3-formylcyclohept-2-en-1-yl)methanesulfonamide in inert solvents forms cyclic dimers, whereas in crystal chain associates are more likely to be formed via hydrogen bonding between the NH and C=O groups of neighboring molecules. The carbonyl group in the title compound undergoes protonation only by the action of very strong trifluoromethanesulfonic acid. Weaker acids give rise to solvate H-complexes at the NH, C=O, and S=O groups. The topology of hydrogen bonds in dimers of different types has been analyzed in terms of the AIM theory.