Microwave assisted synthesis, experimental and theoretical characterization and antibacterial activity screening of novel azomethine compounds containing thiophene and aminophenol functionality.

Emel Ermiş, Atakan Aydın, Hakan Ünver, Suat Sezen, Mehmet Burçin Mutlu

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 2020 Dec 15

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Eight new azomethine compounds (3a-3h) containing thiophene and aminophenol functionality were synthesized in excellent yields by using conventional heating and microwave assisted synthesis methods. The structures of newly synthesized compounds were characterized by spectroscopic techniques such as UV-Vis, FTIR, 1H and 13C NMR and elemental analysis. UV-Vis and 1H NMR results show that all compounds prefer the phenol-imine tautomer form in solvent media. The chemical structure of 3a, 3b and 3g was also confirmed by single crystal X-ray diffraction method. The molecular conformations of 3a, 3b and 3g are stabilized by an N+-H⋯O- type intramolecular hydrogen bond in zwitterionic form in the crystalline solid state. The optimized molecular structures, 1H and 13C NMR chemical shift values, UV-Vis spectroscopic parameters, HOMO-LUMO energies, Mulliken (MPA) and natural (NBO) atomic charges, Natural bond orbitals (NBO), molecular electrostatic potential (MEP) maps and solvent accessible surfaces (SASs) for 3a-3h were calculated by using DFT/B3LYP/6-311G(2d,p) approach. The theoretical spectroscopic features obtained by DFT calculations show a very good agreement with the experimental data. In addition, the synthesized compounds (3a-3h) were screened for their antibacterial activities against Bacillus cereus (NRRL-B3711), Bacillus subtilis (NRRL-B4378), Escherichia coli (NRRL B-3008), Staphylococcus aureus (ATCC-6538) and Salmonella typhimurium (ATCC-13311). The results show that investigated compounds have either moderately active, slightly active or inactive among the tested microorganisms. 3a exhibited the stronger antibacterial activity against all test bacteria than other compounds. It also has been observed that compounds with relatively low HOMO-LUMO energy gaps exhibit better antibacterial effects. Copyright © 2020 Elsevier B.V. All rights reserved.

Citation

Emel Ermiş, Atakan Aydın, Hakan Ünver, Suat Sezen, Mehmet Burçin Mutlu. Microwave assisted synthesis, experimental and theoretical characterization and antibacterial activity screening of novel azomethine compounds containing thiophene and aminophenol functionality. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Dec 15;243:118761