Spectroscopic and Theoretical Studies and Intramolecular Proton Transfer in (Z)-2-Hydroxy-6-(((2-methoxy-5-(trifluoromethyl)phenyl)amino)methylene)cyclohexa-2,4-dien-1-one

Özdemir Tarı G., Kirca B. K., Tasdogan M., Özdemir N., Ağar E.

RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, vol.95, no.8, pp.1621-1631, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 95 Issue: 8
  • Publication Date: 2021
  • Doi Number: 10.1134/s0036024421080252
  • Journal Name: RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Compendex
  • Page Numbers: pp.1621-1631
  • Keywords: X-ray diffraction, quantum mechanical calculations, FT-IR and UV-Vis spectral analysis, GRAPH-SET ANALYSIS, SCHIFF-BASE, FT-IR, OPTICAL-PROPERTIES, DFT CALCULATIONS, METAL-COMPLEXES, FUKUI FUNCTION, NLO, UV, RAMAN
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In present work, a new Schiff base compound, (E)-3-(((2-methoxy-5-(trifluoromethyl)phenyl)imino)methyl)benzene-1,2-diol was synthesized and characterized by X-ray diffraction and spectroscopic methods (FT-IR, UV-Vis) and quantum mechanical calculation methods. The obtained structure is monoclinic, space group P2(1)/c, with unit cell parameters a = 15.1881(10) angstrom, b = 14.5816(11) angstrom, c = 6.2023(5) angstrom, beta = 98.008 (6)degrees, and Z = 4. Theoretical calculations were used to investigate the optimized molecular geometry of the title compound. The calculated and experimental results show the title compound tends to the keto-amine form. Besides, the frontier molecular orbital, non-linear optical properties and electronic structure parameters of the title compound were computed in the solvent media using the theoretical methods. The molecular electrostatic potential surface was obtained at the optimized geometry to predict reactive sites for nucleophilic and electrophilic attack for the studied molecule. Statistical thermodynamic functions for the title compound were calculated at 298.15 K temperature and 1 atm pressure by using the HF and DFT/B3LYP methods with the 6-311++G(d,p) basis set.