Fluorine hydrogen short contacts and hydrogen bonds in substituted benzamides

A series of fluorine substituted benzamides 1-10 was synthesised and investigated by spectroscopic methods (NMR, IR, MS) and X-ray structure analysis. The configuration of these compounds strongly depends on solvent, temperature and substitution pattern. Unexpectedly, some of these compounds form weak intramolecular hydrogen bonds/short N-H center dot center dot center dot F-C contacts in CDCl3 solution and in the solid state. (C) 2009 Elsevier B.V. All rights reserved.