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

Spectrochim Acta A Mol Biomol Spectrosc. 2013 Mar 15;105:563-8. doi: 10.1016/j.saa.2012.12.054. Epub 2013 Jan 2.

Abstract

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 N-H, C-O and C=N 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Guaiacol / analogs & derivatives*
  • Guaiacol / chemistry
  • Models, Molecular
  • Quantum Theory
  • Schiff Bases / chemistry*
  • Spectrophotometry, Infrared

Substances

  • Schiff Bases
  • Guaiacol