Structure and proton-donor ability of N-(1-trifluoromethylsulfonylamino-2,2,2-trichloroethyl)-acrylamide View Full Text


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Article Info

DATE

2009-06

AUTHORS

L. P. Oznobikhina, N. N. Chipanina, B. A. Shainyan, T. N. Aksamentova, E. V. Kondrashov, G. G. Levkovskaya

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. More... »

PAGES

1146

References to SciGraph publications

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  • 2006-04. Structure and intramolecular hydrogen bonds in Bis(trifluoromethylsulfonylamino)methane and N-[(trifluoromethylsulfonyl)aminomethyl]acetamide in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2005-10. Synthesis of N-(1-Sulfonylamino-2-polychloroethyl)acrylamides in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2005-10. Molecular Structure of Complexes with Bifurcated Hydrogen Bond: III. Solvate H-Complexes Formed by Trifluoromethanesulfonamide and Its Cyclic Dimer in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2009-03. Structure and proton-donating ability of trifluoro-N-(2-phenylacetyl)methanesulfonamide in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2005-06. Self-Association of Trifluoromethanesulfonamide in Inert Solvents in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2007-01. Molecular structure of complexes with bifurcated hydrogen bond: IV. Solvate H-complexes of N-methyltrifluoromethanesulfonamide in aprotic protophilic media in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2009-02. Structure and proton donating ability of 2- and 2,5-bis(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)pyrroles in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2004-04. IR Spectra of Trifluoromethanesulfonamide and Its Self-Associates in the Gas Phase in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2007-01. Solvatochromism of heteroaromatic compounds: XXX. N-Methyltrifluoromethanesulfonamide as hydrogen-bond donor in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
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