Conformations and Self-association of Trifluoro-N-(3-formylcyclohept-2-en-1-yl)methanesulfonamide

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...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2014-03, Vol.50 (3), p.337-341
Main Authors: Sterkhova, I. V., Moskalik, M. Yu, Shainyan, B. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary: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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428014030051