title: Modeling the intermolecular interactions: molecular structure of N-3-hydroxyphenyl-4-methoxybenzamide.
abstract: 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.
authors.affiliation: Balıkesir University, Faculty of Science and Literature, Department of Chemistry, 10145 Cagis, Balikesir, Turkey. Electronic address: sedatk@balikesir.edu.tr.
authors.forename: Sedat
authors.initials: S
authors.lastname: Karabulut
authors.affiliation: Balıkesir University, Faculty of Science and Literature, Department of Chemistry, 10145 Cagis, Balikesir, Turkey.
authors.forename: Hilmi
authors.initials: H
authors.lastname: Namli
authors.affiliation: Akdeniz University, Alanya Faculty of Engineering, Materials Science and Engineering, Antalya, Turkey.
authors.forename: Raif
authors.initials: R
authors.lastname: Kurtaran
authors.affiliation: Hacettepe University, Department of Engineering Physics, Beytepe, 06800 Ankara, Turkey.
authors.forename: Leyla Tatar
authors.initials: LT
authors.lastname: Yildirim
authors.affiliation: Jackson State University, Interdisciplinary Nanotoxicology Center, Jackson, MS, USA.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Leszczynski
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D013816:Thermodynamics
chemical_list: D001549:Benzamides
keywords: Amide; DFT; Dimer; Molecular structure; X-ray