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

J Mol Graph Model. 2014 Mar:48:1-8. doi: 10.1016/j.jmgm.2013.11.001. Epub 2013 Nov 28.


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 ¹H NMR, ¹³C NMR and elemental analysis. Molecular structure of the crystal was determined by single crystal X-ray diffraction and DFT calculations. 3 crystallizes in monoclinic P2₁/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.

Keywords: Amide; DFT; Dimer; Molecular structure; X-ray.

MeSH terms

  • Benzamides / chemistry*
  • Computer Simulation
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular*
  • Molecular Conformation
  • Thermodynamics


  • Benzamides