title: H-bond and dipole-dipole interactions between water and COO functional group in methyl benzoate derivatives: Substituent and heteroatom effects.
abstract: Interactions of COOCH3functional group of methyl benzoate (MB) and its derivatives can substantially be affected by substituents and heteroatoms. The substituent and heteroatom effects on the intermolecular interactions in the complexes of MB and its derivatives with the water molecule have been investigated by the quantum mechanical calculations in the present study. Electron donating (ED)/electron withdrawing (EW) substituents increase/decrease the binding energy (ΔEbin) between mentioned functional group and hydrogen bond donor, and the N heteroatom in the six membered ring weakens the effect. The effects of the N heteroatoms depend on their positions in the ring, and the effects of substituents depend on the number and the positions of heteroatoms. Some relations were obtained between the dipole moment of carbonyl group, results obtained from the natural bond orbital (NBO) and the atoms in molecules (AIM) analysis, binding energy and Hammett constants of substituents. The results can be used to predict the factors affect the intermolecular interactions, and to improve the ligand-protein bindings in biological systems.
authors.affiliation: Department of Chemistry, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran.
authors.forename: S
authors.initials: S
authors.lastname: Sarhadinia
authors.affiliation: Department of Chemistry, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran. Electronic address: ebrahimi@chem.usb.ac.ir.
authors.forename: A
authors.initials: A
authors.lastname: Ebrahimi
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D006860:Hydrogen Bonding; D007700:Kinetics; D008958:Models, Molecular; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
chemical_list: D001565:Benzoates; D014867:Water; C044605:methyl benzoate
keywords: Ab initio method; Drug design; Methyl benzoate; Methyl nicotinate; Methyl picolinate; Population analysis