Experimental and computational studies on (Z)-1-((4-phenylamino)phenylamino)-methylene)naphthalen-2(1H)-one

Alpaslan G., Macit M., Erdoenmez A., Bueyuekguengoer O.

STRUCTURAL CHEMISTRY, cilt.22, sa.3, ss.681-690, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 22 Sayı: 3
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1007/s11224-011-9745-8
  • Dergi Adı: STRUCTURAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.681-690
  • Anahtar Kelimeler: Schiff base, DFT, HF, NBO, Non-linear optical, NONLINEAR-OPTICAL PROPERTIES, INITIO MOLECULAR POTENTIALS, DENSITY-FUNCTIONAL THEORY, SCHIFF-BASES, SOLID-STATE, EQUILIBRIUM GEOMETRIES, EXCITATION-ENERGIES, PROTON-TRANSFER, TAUTOMERISM, CONTINUUM
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The Schiff base compound (Z)-1-((4-phenylamino)phenylamino)methylene)naphthalen-2(1H)-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 Hartree-Fock (HF) and density functional method (B3LYP) with 6-31G(d,p) basis set. Calculated results show that density functional theory DFT and HF can well reproduce the structure of the title compound. Using the time-dependent density functional theory (TD-DFT) and Hartree-Fock (TD-HF) methods, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and experimental ones is determined. 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 polarizable continuum model (PCM). The total energy of the title compound decreases with increasing polarity of the solvent. In addition, DFT calculations of the title compound, molecular electrostatic potential (MEP), natural bond orbital analysis (NBO), and non-linear optical (NLO) properties were performed at B3LYP/6-31G(d,p) level of theory.