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


Alpaslan Y. B. , Suleymanoglu N., Oztekin E., Ersahin F., Agar E., Isik S.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol.40, no.11, pp.950-956, 2010 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 40 Issue: 11
  • Publication Date: 2010
  • Doi Number: 10.1007/s10870-010-9769-8
  • Journal Name: JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.950-956
  • Keywords: Crystal structure, Schiff-base, AM1, PM3, PM6, DFT, CRYSTAL-STRUCTURE, COMPLEXES

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) A(3) 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)degrees 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 degrees to +180 degrees in every 10 via PM3 semi-empirical method