Modeling the intermolecular interactions: Molecular structure of N-3-hydroxyphenyl-4-methoxybenzamide

Karabulut S., Namli H., Kurtaran R., Yildirim L. T., Leszczynski J.

JOURNAL OF MOLECULAR GRAPHICS & MODELLING, vol.48, pp.1-8, 2014 (SCI-Expanded) identifier identifier identifier


The title compound, N-3-hydroxyphenyl-4-methoxybenzamide (3) was prepared by the acylation reaction of 3-aminophenol (1) and 4-metoxybenzoylchloride (2) in THF and characterized by H-1 NMR, C-13 NMR and elemental analysis. Molecular structure of the crystal was determined by single crystal X-ray diffraction and DFT calculations. 3 crystallizes in monoclinic P2(1)/c space group. The influence of intermolecular interactions (dimerization and crystal packing) on molecular geometry has been evaluated by calculations performed for three different models; monomer (3), dimer (4) and dimer with added unit cell contacts (5). Molecular structure of 3, 4 and 5 was optimized by applying B3LYP method with 6-31G+(d,p) basis set in gas phase and compared with X-ray crystallographic data including bond lengths, bond angles and selected dihedral angles. It has been concluded that although the crystal packing and dimerization have a minor effect on bond lengths and angles, however, these interactions are important for the dihedral angles and the rotational conformation of aromatic rings. (C) 2013 Elsevier Inc. All rights reserved.