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

Article abstract of DOI:10.1016/j.molstruc.2012.05.059

In this work, the structure of N′-(2-methoxy-benzylidene)-N-[4-(3- methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-chloro-acetic hydrazide, (C ₂₄H₂₄ClN₃O₂S), 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 na2₁ with a = 14.4170 (4) A, b = 11.5441 (4) A, c = 27.8420 (8) A 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.