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The conformations of new CF3 and CF3-CHF containing amides derived from carbohydrates: NMR, crystallographic and DFT study

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Abstract

A new convenient synthetic procedure for the preparation of tri- and tetrafluoropropanamides derived from sugars has been described. The conformations of fluorinated amides calculated for isolated molecules and those in the crystal state have been compared. In contrast to single α-fluorine substituted amides, which preferred the anti conformation around the F–C–C[double bond, length as m-dash]O bond, for tetrafluorinated amides the additional trifluoromethyl group forces the conformation of the F–C–C[double bond, length as m-dash]O bond to be nearly syn.

Graphical abstract: The conformations of new CF3 and CF3-CHF containing amides derived from carbohydrates: NMR, crystallographic and DFT study

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Publication details

The article was received on 11 Aug 2017, accepted on 13 Sep 2017 and first published on 18 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ02986A
Citation: New J. Chem., 2017, Advance Article
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    The conformations of new CF3 and CF3-CHF containing amides derived from carbohydrates: NMR, crystallographic and DFT study

    M. Bilska-Markowska, T. Siodla, E. Patyk-Kaźmierczak, A. Katrusiak and H. Koroniak, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02986A

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