Comparative experimental and theoretical studies of N-(4-Methylbenzylidene)-N′-(2-carboxyphenyl) hydrazine novel Schiff base

Abstract

In this work, N-(4-Methylbenzylidene)-N′-(2-carboxyphenyl) hydrazine, C15H14N2O2, Schiff base molecule has been synthesized and characterized by elemental analyses, UV–Vis and IR spectroscopy and single crystal X-ray determination. The molecule of the title compound adopt an E configuration about the azomethine CN double bond. The benzene and phenyl rings are planar and the dihedral angle between the planes is 7.2(2)°. The crystal structure is stabilized by intermolecular OH⋯O and intramoleculer NH⋯O hydrogen bonding interactions. X-ray diffraction analyses show that, N-(4-Methylbenzylidene)-N′-(2-carboxyphenyl) hydrazine Schiff base molecule crystallizes in the monoclinic system, P21/c space group, a=4.392(5)Å, b=22.340(5)Å, c=13.528(5)Å, β=92.882(5)°, V=1325.7(16)Å3, Z=4. The conformational analysis of N-(4-Methylbenzylidene)-N′-(2-carboxyphenyl) hydrazine was performed by the density functional theory (DFT) B3LYP method using the 6-311++G(d,p) basis set. Also, theoretical values of FTIR and UV–Vis were performed by the same method. The calculated geometry parameters, IR and UV–Vis results were compared with experimental results.