Microwave-assisted synthesis, characterizations, antimicrobial activities, and DFT studies on some pyridine derived Schiff bases


Ayaz M., Gündoğdu Ö., Aytaç S., Erdem B., Çiftçi H., ERDOĞDU Y.

Journal of Molecular Structure, cilt.1269, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1269
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.molstruc.2022.133791
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Schiffbases, Microwave synthesis, Characterizations, Antimicrobial activities, DFT
  • Gazi Üniversitesi Adresli: Evet

Özet

© 2022 Elsevier B.V.This study reports a joint experimental, theoretical and microbiological investigation on the (E)-N,N-dimethyl-4-((pyridine-2-ylmethylene)amino)aniline (5), (E)-N,N-dimethyl-4-((pyridine-4-ylmethylene)amino)aniline (6) and (E)-N,N-dimethyl-4-((pyridine-3-ylmethylene)amino)aniline (7). These compounds were synthesized with microwave method and their structures characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analysis tecniques. In the theoretical studies, torsional barriers analysis, ground state structure, Fourier Transform Infrared spectra (FT-IR), and Nuclear Magnetic Resonance spectra (NMR) of 5, 6, and, 7 were calculated by Density Functional Theory (DFT) computations. The conformers obtained from the torsional barrier scanning were optimized by B3LYP/6-31G(d,p) level. The harmonic vibrational frequencies, potential energy distribution (PED), infrared intensities, and NMR chemical shifts of the most stable conformers were determined using the B3LYP/6-311++G(d,p). Theoretically, predicted spectral data were compared with experimental results. Antimicrobial studies of the synthesized compounds were performed against various microbial strains. Antimicrobial activities of 5, 6, and, 7 were tested against selected bacteria and yeast through minimum inhibitory concentration (MIC) and diffusion method. Compound 7 was found to be the most active against bacteria and yeast, while compound 5 was found to be moderately active. Compounds 6 (against S. aureus and C. albicans) and, 7 were found to have a very high minimum inhibitory concentration, ranging between 1.95 and 7.81 g/mL (against P. aeruginosa and E. coli). Compounds (6 and 7) showed zone of inhibition values in the range of 10–20 mm against other bacteria except L. monocytogenes and S. thyphimurium.