Experimental and Semi-Empirical and DFT Calculational Studies on (E)-2-[(2,4-Dichlorophenylimino) methyl]-p-cresol

Abstract

The molecular and crystal structure of the title compound, C14H11Cl2NO, has been determined by X-ray single crystal diffraction technique. The compound crystallizes in the orthorhombic, space group Pbca with unit cell dimensions a = 7.5537(10) A, b = 11.5518(13) A, c = 29.760(4) A, M r  = 280.14, V = 2596.8(6) A3, Z = 8, R 1 = 0.065 and wR 2 = 0.191. The title compound exists in the enol–imine tautomeric form with a strong intramolecular O–H···N hydrogen bond. The dihedral angle between the two benzene rings is 37.66(15)°. The asymmetric unit in the crystal structure contains only one neutral molecule. Calculational studies were performed by using AM1, PM3, PM6 semi-empirical and DFT methods. Geometry optimizations of compound have been carried out by using three semi-empirical methods and DFT method and bond lengths, bond and torsion angles of title compound have been determined. Dipole moments (Debye) and the energy parameters of compound (kcal/mol) were calculated by using above mentioned calculation methods. Atomic charge distribution has been obtained from AM1, PM3, PM6 and DFT. In order to determine conformational flexibility on the molecule, molecular energy profile of the title compound was obtained with respect to the selected torsion angle T(N1–C7–C1–C2), which is varied from −180° to +180° in every 10 via PM3 semi-empirical method. A new crystal of (E)-2-[(2,4-Dichlorophenylimino) methyl]-p-cresol with orthorhombic space group Pbca [unit cell dimensions a = 7.5537(10) A, b = 11.5518(13) A, c = 29.760(4) A, V = 2596.8(6) A3, Z = 8, R 1 = 0.065] has been determined by single crystal X-ray diffraction study and theoretical calculations were performed by using AM1, PM3, PM6 semi-empirical and DFT methods.