The intramolecular hydrogen bond in 2-hydroxy-benzamides

The two crystal structures of 5-chloro-2-hydroxy-benzamide and 2-hydroxy-N,N-diethyl-benzamide were determined by X-ray diffraction at 100 K. The intramolecular and intermolecular hydrogen bonds were found in these structurally similar 2-hydroxy-benzamides. Analysis of the hydrogen bonding was carried out on the basis of X-ray data, infrared spectra, and DFT calculations. Disruption of the intramolecular hydrogen bonding in the solid state by a steric effect is shown. Conformational analysis and potential energy calculations as functions of the turning angle around the Caryl–Calkyl bond were conducted. The values obtained for the HOMA index indicate mutual compensation of the amide and hydroxyl groups (due to the high degree aromaticity of the phenyl ring).