Issue 21, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Aug 2017
Accepted
13 Sep 2017
First published
18 Sep 2017

New J. Chem., 2017,41, 12631-12644

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, 41, 12631 DOI: 10.1039/C7NJ02986A

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