N '-(2-methoxy-benzylidene)-N-[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-chloro-acetic hydrazide: X-ray structure, spectroscopic characterization and DFT studies

Inkaya E., Dincer M., Ekici O., ÇUKUROVALI A.

JOURNAL OF MOLECULAR STRUCTURE, vol.1026, pp.117-126, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1026
  • Publication Date: 2012
  • Doi Number: 10.1016/j.molstruc.2012.05.059
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.117-126
  • Keywords: X-ray structure determination, IR and NMR spectroscopy, DFT calculations, Cyclobutane, Non-linear optical properties, NONLINEAR-OPTICAL PROPERTIES, DENSITY-FUNCTIONAL-THEORY, SCHIFF-BASE LIGANDS, HARTREE-FOCK, COMPLEXES, DERIVATIVES, POTENTIALS, GEOMETRIES, 2ND-ORDER, CONTINUUM
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In this work, the structure of N'-(2-methoxy-benzylidene)-N-[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-chloro-acetic hydrazide, (C24H24ClN3O2S), was characterized by X-ray single crystal diffraction technique, IR-NMR spectroscopy and quantum chemical computational methods as both experimental and theoretically. The compound crystallizes in the orthorhombic space group P na2(1) with a = 14.4170 (4) angstrom, b = 11.5441(4) angstrom, c = 27.8420 (8) angstrom and Z = 8. X-ray study shows that crystal has two independent molecules in the asymmetric unit. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) basis set and compared with the experimental data. To determine conformational flexibility, molecular energy profile of the tittle compound was obtained by semi-empirical (AM1) with respect to selected degree of torsional freedom, which was varied from -180 degrees to + 180 degrees in steps 10. From the optimized geometry of the molecule, vibrational frequencies, gauge-independent atomic orbital (GIAO) H-1 and C-13 NMR chemical shift values, molecular electrostatic potential (MEP) distribution, non-linear optical properties, frontier molecular orbitals (FMOs) of the title compound have been calculated in the ground state theoretically. (C) 2012 Elsevier B.V. All rights reserved.