Theoretical and experimental investigation of (E)-2-([3,4-dimethylphenyl)imino]methyl)-3-methoxyphenol: Enol-keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis

Demircioglu Z., Albayrak C., Buyukgungor O.

JOURNAL OF MOLECULAR STRUCTURE, vol.1065, pp.210-222, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1065
  • Publication Date: 2014
  • Doi Number: 10.1016/j.molstruc.2014.02.062
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.210-222
  • Keywords: Natural population analysis (NPA), Density functional theory (DFT), Nonlinear optical properties (NLO), Natural bond analysis (NBO), Mulliken electronegativity, DENSITY-FUNCTIONAL THEORY, NONLINEAR-OPTICAL RESPONSE, MOLECULAR-ORBITAL METHODS, AB-INITIO CALCULATION, FT-RAMAN SPECTRA, VIBRATIONAL-SPECTRA, SCHIFF-BASES, EXCITATION-ENERGIES, HARTREE-FOCK, SOLID-STATE
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The molecular structure and spectroscopic properties of (E)-2-([3,4-dimethylphenyl)iminolmethyl)-3methoxyphenol were investigated by X-ray diffraction, FT-IR and UV-vis spectroscopy. The vibrational frequencies calculatedusing DFT/B3LYP/6-31G(d,p) method. Results showed better agreement with the experimental values. The electronic properties was studied and the most prominent transition corresponds to pi ->pi* and pi ->pi*. Two types of intramolecular hydrogen bonds are strong O-H center dot center dot center dot N interactions in enol-imine form and N-H center dot center dot center dot O interactions in keto-amine form are compared by using density functional theory (DFT) method with B3LYP applying 6-31G(d,p) basis set. Both enol-keto tautomers engender six-membered ring due to intramolecular hydrogen bonded interactions.