Synthesis, spectroscopic and X-ray structural characterization, quantum chemical studies and investigation of gama-irradiated effects of the novel hydrazone compound: [(E)-3-(2-nitrophenyl)-(E)-1-(2-phenylhydrazono)]-1-phenylallylidene

Abstract

The novel hydrazone compound, [(E)-3-(2-nitrophenyl)-(E)-1-(2-phenylhydrazono)]-1-phenylallylidene (2), has been synthesized, characterized by FTIR, 1H NMR, 13C NMR techniques, elemental analysis, X-ray structure analysis and has been investigated gama-irradiated effect. Additionally, the molecular geometrical parameters, frontier molecular orbital energies (HOMO, LUMO), their energy gap (ΔE), molecular electrostatic potential analysis of the compound have been calculated by using DFT/B3LYP with 6-311G (d, p) level. Also, IR frequencies, 1H and 13C NMR chemical shifts of the compound were calculated by using DFT calculations at the same level basis and changing in lattice parameters, unit cell volume and density of the compound are observed after gama irradiated at XRD data. Unirradiated state of the title compound (C21H17N3O2) crystallizes in the monoclinic space group P21/n with a = 9.1782(7) Å, b = 16.1359(12) Å, c = 11.9709(12) Å, β = 101.022(8)o, V = 1740.2(3) Å3, Dcalc = 1.3106 g/cm3 and Z = 4 while irradiated state of title compound showed significant changes in lattice parameters, crystal volume and density. In contrast, the crystal system is found to be the same at after and before irradiation. The calculated geometrical parameters, IR frequencies, 1H and 13C NMR chemical shifts of the compound were in good agreement with the observed single crystal- XRD data, IR, 1H and 13C NMR spectra.