Computational and spectroscopic studies of a new Schiff base 3-hydroxy-4-methoxybenzylidene(2-hydroxyphenyl)amine and molecular structure of its corresponding zwitterionic form

Computational and spectroscopic properties of a novel Schiff base compound, 3-hydroxy-4-methoxybenzylidene(2-hydroxyphenyl)amine were studied. The crystal structures of the title compound and its corresponding zwitterionic form were analyzed by X-ray diffraction. The presence of NH, CO and CN stretching vibrations in IR spectrum strongly suggest that the title compound has zwitterionic form in the solid state. Molecular geometry of the title compound in the ground state has been calculated using the density functional method (DFT) at B3LYP 6-31++G(d,p) basis set and was compared with the experimental data. The calculated results of the title compound show that the optimized geometry can well reproduce the crystal structure. The molecule shows absorption bands at 345 and 363 nm in EtOH. The shoulder-shaped bands at 415 nm can be assigned to n → π* transitions. The absorption band is observed at 285 nm in EtOH corresponds to the π → π* transitions.

Graphical abstractSpectroscopic properties of a new Schiff base 3-hydroxy-4-methoxybenzylidene(2-hydroxyphenyl)amine and molecular structure of its corresponding zwitterionic form were studied. Computational and experimental results were compared. The crystal structures of the title compound and the corresponding zwitterionic form were analyzed by X-ray diffraction.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Spectroscopic properties of a novel Schiff base is studied. ► Computational of a new ligand was studied. ► The crystal structure of the compound and its zwitterionic form were analyzed.