Experimental and quantum chemical calculational studies on 2-[(4-propylphenylimino)methyl]-4-nitrophenol

Alaman Ağar A., Tanak H., Yavuz M.

MOLECULAR PHYSICS, cilt.108, sa.13, ss.1759-1772, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 108 Sayı: 13
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1080/00268976.2010.490793
  • Dergi Adı: MOLECULAR PHYSICS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1759-1772
  • Anahtar Kelimeler: Schiff base, vibrational assignment, density functional theory, Hartree-Fock, electronic absorption spectra, DENSITY-FUNCTIONAL-THEORY, INTRAMOLECULAR PROTON-TRANSFER, NONLINEAR-OPTICAL PROPERTIES, AB-INITIO CALCULATIONS, SCHIFF-BASE COMPLEXES, HARTREE-FOCK, ELECTROSTATIC POTENTIALS, EQUILIBRIUM GEOMETRIES, EXCITATION-ENERGIES, TAUTOMERISM
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The Schiff base compound 2-[(4-propylphenylimino)methyl]-4-nitrophenol has been synthesized and characterized by IR, UV-Vis, and X-ray single-crystal determination. The molecular geometry from X-ray determination of the title compound in the ground state has been compared using the Hartree-Fock (HF) and density functional theory (DFT) with the 6-31G(d) basis set. The calculated results show that the DFT and HF can well reproduce the structure of the title compound. The energetic behaviour of the title compound in solvent media was examined using the B3LYP method with the 6-31G(d) basis set by applying the Onsager and the polarizable continuum model (PCM). The results obtained with these methods reveal that the PCM method provides a more stable structure than Onsager's method. Using the TD-DFT method, electronic absorption spectra of the title compound have been predicted and good agreement with the TD-DFT method and the experimental determination was found. The predicted nonlinear optical properties of the title compound are much greater than those of urea. In addition, DFT calculations of the molecular electrostatic potential and NBO analysis of the title compound were carried out at the B3LYP/6-31G(d) level of theory.