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

• Published in: Journal of molecular structure Vol. 1168; pp. 115 - 126
• Main Authors: Ermiş, Emel, Durmuş, Kaan, Aygüzer, Ömer Uğur, Berber, Halil, Güllü, Mustafa
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.09.2018
• Subjects: 2,2′-Oxydianiline; 2-Hydroxy-5-(thiophen-2-yl)benzaldehyde; Density functional theory (DFT); NMR chemical shifts; Vibrational spectroscopy; 2,2′-Oxydianiline; NMR chemical shifts; 2-Hydroxy-5-(thiophen-2-yl)benzaldehyde; Density functional theory (DFT); Vibrational spectroscopy
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2018.05.021

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, 1H and 13C NMR spectroscopic results and elemental analysis. The optimized molecular geometry, sum of electronic and thermal free energies (SETFEs), dipole moment, IR frequencies, 1H and 13C 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). •A new symmetrical azomethine compound was successfully synthesized and characterized.•The theoretical calculations were performed using the DFT/B3LYP level of 6-311 + G(d,p) basis set.•The theoretical results were compared with the experimentally obtained spectroscopic data.•SETFE, atomic charges, MEP and HOMO-LUMO energies of the compound were also investigated by DFT.