Structure and proton-donor ability of N-(1-trifluoromethylsulfonylamino-2,2,2-trichloroethyl)-acrylamide |
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| Authors: | L. P. Oznobikhina N. N. Chipanina B. A. Shainyan T. N. Aksamentova E. V. Kondrashov G. G. Levkovskaya |
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| Affiliation: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia |
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| Abstract: | Quantum-chemical calculations (B3LYP/6-311G**) of N-(1-trifluoromethylsulfonylamino-2,2,2-trichloroethyl)acrylamide CF3SO2NHCH(CCl3)NHC(O)CH=CH2 (I) in the isolated state revealed four local minima corresponding to the conformers with the syn- and antiperiplanar orientation of the C=O and N-H bonds in the amide fragment, two of which containing the intramolecular C(O)NH…O=S or SO2NH…O=C hydrogen bonds. Judged from the data of IR spectroscopy and dielectrometry, compound I in inert media exists predominantly in the form of conformer with antiperiplanar amide fragment and free NH group. Its self-associates in molecular crystals and solutions are formed by hydrogen bonds SO2NH…O=C. Spectroscopic acidity of compound I determined as the value of Δν(NH) upon interactions with DMF in CCl4 is higher than that of N-methyltrifluoromethanesulfonamide. |
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