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

Mohammad Hossein Habibi, Elahe Shojaee, Mahnaz Ranjbar, Hamid Reza Memarian, Akihiko Kanayama, Takayoshi Suzuki

Research output: Contribution to journalArticle

17 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)563-568
Number of pages6
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume105
DOIs
Publication statusPublished - Mar 15 2013

Fingerprint

Schiff Bases
Molecular structure
imines
Amines
Absorption spectra
amines
molecular structure
Crystal structure
absorption spectra
crystal structure
zwitterions
Geometry
Carbon Monoxide
shoulders
Electron transitions
geometry
Ground state
Stretching
solid state
X ray diffraction

Keywords

  • DFT study
  • Intramolecular proton transfer
  • Schiff base
  • Zwitterionic

ASJC Scopus subject areas

  • Instrumentation
  • Atomic and Molecular Physics, and Optics
  • Analytical Chemistry
  • Spectroscopy

Cite this

Computational and spectroscopic studies of a new Schiff base 3-hydroxy-4-methoxybenzylidene(2-hydroxyphenyl)amine and molecular structure of its corresponding zwitterionic form. / Habibi, Mohammad Hossein; Shojaee, Elahe; Ranjbar, Mahnaz; Memarian, Hamid Reza; Kanayama, Akihiko; Suzuki, Takayoshi.

In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, Vol. 105, 15.03.2013, p. 563-568.

Research output: Contribution to journalArticle

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AB - 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.

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