Experimental and molecular modeling investigation of (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide

Ozdemir N., DAYAN S., DAYAN O., Dincer M., Kalaycioglu N.

MOLECULAR PHYSICS, cilt.111, sa.6, ss.707-723, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 111 Sayı: 6
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1080/00268976.2012.742209
  • Dergi Adı: MOLECULAR PHYSICS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.707-723
  • Anahtar Kelimeler: crystal structure, IR, NMR and Uv-vis spectroscopy, density functional theory, enol-imine, keto-amine tautomerism, solvent effects, INTRAMOLECULAR PROTON-TRANSFER, NONLINEAR-OPTICAL PROPERTIES, DENSITY-FUNCTIONAL THEORY, AB-INITIO, TAUTOMERIC EQUILIBRIUM, SCHIFF-BASES, SOLID-STATE, EFFICIENT IMPLEMENTATION, TRANSFER HYDROGENATION, ELECTRONIC-PROPERTIES
  • Erciyes Üniversitesi Adresli: Evet

Özet

The Schiff base compound (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide has been synthesized and characterized by IR, NMR and Uv-vis spectroscopies, and single-crystal X-ray diffraction technique. In addition, quantum chemical calculations employing density functional theory (DFT) method with the 6311++G(d,p) basis set were performed to study the molecular, spectroscopic and some electronic structure properties of the title compound, and the results were compared with the experimental findings. There exists a good correlation between experimental and theoretical data. Enol-imine/keto-amine tautomerization mechanism was investigated in the gas phase and in solution phase using the polarizable continuum model (PCM) approximation. The energetic and thermodynamic parameters of the enol-imineketo-amine transfer process show that the single proton exchange is thermodynamically unfavored both in the gas phase and in solution phase. However, the reverse reaction seems to be feasible with a low barrier height and is supported by negative values in enthalpy and free energy changes both in the gas phase and in solution phase. The solvent effect is found to be sizable with increasing polarity of the solvents for the reverse reaction. The predicted nonlinear optical properties of the compound are found to be much greater than those of urea.