Molecular structure and density functional modelling studies of 2-[(E)-2-(4-hydroxyphenyl)ethyliminomethyl]phenol

Zeyrek C. T., BİLGE KOÇAK S., ÜNVER H., Pektas S., Basterzi N. S., ÇELİK Ö.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1100, ss.570-581, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1100
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.molstruc.2015.07.068
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.570-581
  • Anahtar Kelimeler: Schiff base, PES scan, Density functional theory, Spectroscopy, Nonlinear optical effects, NONLINEAR-OPTICAL PROPERTIES, DINUCLEAR IRON(III) COMPLEX, AB-INITIO CALCULATIONS, CRYSTAL-STRUCTURE, SCHIFF-BASES, SPECTROSCOPIC PROPERTIES, EQUILIBRIUM GEOMETRIES, EXCHANGE INTERACTION, MAGNETIC-PROPERTIES, FT-IR
  • Ankara Üniversitesi Adresli: Evet

Özet

In the present work, the tautomerism in 2-[(E)-2-(4-hydroxyphenyl)ethyliminomethyl]Phenol was investigated by experimental (MS, FT-IR, NMR and X-ray diffraction) and computational method [density functional theory (DFT)]. The optimized geometrical structures, atomic charges, molecular electrostatic potential (MEP), natural bond orbital (NBO) and nonlinear optical (NLO) effects of the compound have been investigated by using DFT calculations. The potential energy surface (PES) scans about three important torsion angles are performed by using B3LYP/6-311+-FG (d,p) level of theoretical approximation for the compound. The experimental (FT-IR) and calculated vibrational frequencies (using DFT) of the title compound have been compared. The H-1 and C-13 NMR chemical shift assignments have been performed using DFT. To investigate the tautomeric stability, some properties such as total energy, HOMO and LUMO energies of the compound were obtained at B3LYP and B1B95/6-311++G(d,p) level in the gas phase. The calculated results showed that the phenol-imine form of the compound was more favorite than keto-amine form. Moreover, a good correlation between experimental and theoretical data for phenol-imine form of the compound was found. (C) 2015 Elsevier B.V. All rights reserved.