4-Hydroxy-N′-[(1E)-1-(4-methylphenyl)ethylidene]benzohydrazide: Synthesis, crystal structure, and spectroscopic studies

Abstract

The titled compound has been synthesized by reaction of 4′-methylacetophenon with 4-hydrox-ybenzohydrazide in presence of catalytic amount of glacial acetic acid. The compound is characterized by elemental analysis, IR, 1H NMR, 13C NMR and UV-visible spectra. The crystal structure was determined by X-ray diffraction method. Both X-ray data and NMR spectra indicate that the molecule exists in a trans configuration with respect to the C=N bond. The observation of strong ν(C=O) peak in IR spectra of the aroylhydrazone compound suggests that it is in keto form in solid state. X-ray diffraction results confirm this suggestion. In the crystal structure, there are N-H...O and O-H...O hydrogen bonds and weak C-H...π interaction.