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

Abstract

In this work, the structure of N′-(2-methoxy-benzylidene)-N-[4-(3- methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-chloro-acetic hydrazide, (C <inf>24</inf>H <inf>24</inf>ClN <inf>3</inf>O <inf>2</inf>S), 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 <inf>1</inf> with a = 14.4170 (4) Å, b = 11.5441 (4) Å, c = 27.8420 (8) Å 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° to +180° in steps 10°. From the optimized geometry of the molecule, vibrational frequencies, gauge-independent atomic orbital (GIAO) 1H and 13C 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. © 2012 Elsevier B.V. All rights reserved.