Combined Experimental and Computational Modeling Studies on 4-[(2-Hydroxy-3-methylbenzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Tanak H., Alaman Ağar A., Yavuz M.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, cilt.111, sa.9, ss.2123-2136, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 111 Sayı: 9
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1002/qua.22504
  • Dergi Adı: INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2123-2136
  • Anahtar Kelimeler: density functional theory, molecular electrostatic potential, NBO, PCM, TD-DFT, DENSITY-FUNCTIONAL THEORY, NONLINEAR-OPTICAL PROPERTIES, INITIO MOLECULAR POTENTIALS, SCHIFF-BASE COMPLEXES, ELECTROSTATIC POTENTIALS, EQUILIBRIUM GEOMETRIES, EXCITATION-ENERGIES, HARTREE-FOCK, SOLID-STATE, TAUTOMERISM
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The Schiff base compound, 4-[(2-hydroxy-3-methylbenzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, has been synthesized and characterized by IR, UV-vis, and X-ray single-crystal determination. Molecular geometry from X-ray experiment of the title compound in the ground state have been compared using the density functional method (B3LYP) with 6-31G(d,p) basis set. Calculated results show that density functional theory (DFT) can well reproduce the structure of the title compound. The energetic behavior of the title compound in solvent media has been examined using B3LYP method with the 6-31G(d,p) basis set by applying the Onsager and the polarizable continuum model (PCM). The results obtained with these methods reveal that the PCM method provided more stable structure than Onsager's method. By using TD-DFT method, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and the experimental one is determined. The predicted nonlinear optical properties of the title compound are much greater than ones of urea. In addition, DFT calculations of the title compound, molecular electrostatic potential and NBO analysis were performed at B3LYP/6-31G(d,p) level of theory. (C) 2010 Wiley Periodicals, Inc. Int J Quantum Chem 111: 2123-2136, 2011