Synthesis, crystal structure analysis, biological activity and molecular docking studies of (E)-4-amino-N'-(1-phenylethylidene)benzohydrazide

Abstract

• ( E )−4-Amino-N'-(1-phenylethylidene) benzohydrazide have been synthesized and characterized by physical, spectral and analytical data. • Intermolecular interactions in the crystal packing have been studied. • IR and NMR spectra, DFT analysis and frontier molecular orbitals have been studied. • Antimicrobial and docking studies have been carried out. ( E )-4-Amino-N'-(1-phenylethylidene) benzohydrazide ( 4-APEBH ) is synthesized by condensing 4-aminobenzohydrazide with acetophenone in the molar ratio of 1:1 using methanol as solvent .Structural elucidation of 4-APEBH have been carried out using single crystal X-ray crystallography, FT-IR, 1 H NMR and 13 C NMR spectra. X-ray analysis of 4 -APEBH shows that the compound exists in E- configuration about azomethine double bond. DFT calculations using B3LYP/6-311 ++ G method have been carried out for 4-APEBH to get the optimized geometry, IR and NMR frequencies and energies of HOMO – LUMO. Antimicrobial activity and docking studies of 4-APEBH revealed that the molecule posses antibacterial activity and the ability of drug resistance, respectively.