Abstract
According to the data of quantum-chemical calculations and IR spectroscopy the trifluoro-N-(2-phenylacetyl)methanesulfonamide CF3SO2NHC(O)CH2Ph in the isolated state and in inert media exists in the form of two conformers with the syn- and antiperiplanar orientation of the C=O and N-H bonds. Its self-associates in the CCl4 solution and in molecular crystals constitute cyclic dimers formed by the NH···O=S bonds and chain dimers with the NH···O=C bonds. As a hydrogen bond donor, trifluoro-N-(2-phenylacetyl)methanesulfonamide is stronger than N-methyltrifluoromethanesulfonamide. Its pKa in methanol is 5.45, that is 5 pK units lower than for amides CF3SO2NHR and 2 pK units higher than for imide (CF3SO2)2NH.
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