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 NH⋯FC contacts in CDCl3 solution and in the solid state.

Graphical abstractA series of fluorine substituted benzamides was synthesised and investigated by spectroscopic methods 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 NH⋯FC contacts in CDCl3 solution and in the solid state.Figure optionsDownload full-size imageDownload as PowerPoint slide