A new 2,2 '-oxydianiline derivative symmetrical azomethine compound containing thiophene units: Synthesis, spectroscopic characterization (UV-Vis, FTIR, H-1 and C-13 NMR) and DFT calculations

Ermis E., Durmus K., Ayguzer O. U., BERBER H., GÜLLÜ M.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1168, ss.115-126, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1168
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.molstruc.2018.05.021
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.115-126
  • Anahtar Kelimeler: 2-Hydroxy-5-(thiophen-2-yl)benzaldehyde, 2,2 '-Oxydianiline, Vibrational spectroscopy, NMR chemical shifts, Density functional theory (DFT), SCHIFF-BASE, MOLECULAR DOCKING, SOLAR-CELLS, COMPLEXES, PERFORMANCE, CHEMISTRY, DENSITY, IR, ANTIBACTERIAL, TAUTOMERISM
  • Ankara Üniversitesi Adresli: Evet

Özet

In this study, a new symmetrical azomethine compound, N,N'-oxydiphenylenebis(5-(thiophen-2-yl) salicylidenimine OPBTS (5), having two thiophene rings and N, O donor groups, was successfully prepared by a simple condensation reaction of 2-hydroxy-5-(thiophen-2-yl)benzaldehyde (3) and 2,2'-oxydianiline (4). Characterization of OPBTS was performed by the analysis of UV-Vis., FTIR, H-1 and C-13 NMR spectroscopic results and elemental analysis. The optimized molecular geometry, sum of electronic and thermal free energies (SETFEs), dipole moment, IR frequencies, H-1 and C-13 NMR chemical shift values, UV-Vis. spectroscopic parameters, HOMO-LUMO energies, molecular electrostatic potential (MEP) map and atomic charges of OPBTS were calculated by using Density Functional Theory (DFT/B3LYP/6-311 + G(d, p)) method in the gas phase and various solvents. The theoretical results were compared to the experimentally obtained data and all results were found to be compatible. The experimental and theoretical results confirmed the proposed molecular structure for the new synthesized bis-azomethine derivative (OPBTS). (C) 2018 Elsevier B.V. All rights reserved.