Structure and proton-donating ability of trifluoro-N-(2-phenylacetyl)methanesulfonamide View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2009-03

AUTHORS

L. P. Oznobikhina, N. N. Chipanina, L. L. Tolstikova, A. V. Bel’skikh, V. A. Kukhareva, B. A. Shainyan

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. More... »

PAGES

435-443

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070363209030165

DOI

http://dx.doi.org/10.1134/s1070363209030165

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1038661464


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