Symmetrical Schiff Bases of Phtaldehyde: Synthesis, Experimental and DFT Characterization as well as Antibacterial Activity
نویسندگان
1 Department of Chemistry, Ma. C., Islamic Azad University, Mashhad, I.R. IRAN
2 Department of Chemistry, Ma. C., Islamic Azad University, Mashhad, I.R. IRAN
3 Department of Chemistry, Ma. C., Islamic Azad University, Mashhad, I.R. IRAN
4 Department of Chemistry, Ma. C., Islamic Azad University, Mashhad, I.R. IRAN
5 Department of Chemistry, Ma. C., Islamic Azad University, Mashhad, I.R. IRAN
doi
10.30492/ijcce.2025.2063899.7159چکیده
Two symmetrical Schiff bases, formed by condensing meta- and para-phthalaldehydes with 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol, were synthesized and characterized using NMR, IR, mass spectrometry, UV-Vis, fluorescence, and elemental analysis. Complementary DFT calculations were used to determine optimized geometries, structural parameters, tautomerism, frontier orbitals, and spectral properties. The congruence between experimental values and calculated IR and NMR data confirms the accuracy of the optimized geometries of both Schiff bases. Both synthesized Schiff bases possess symmetrical and planar geometries. Bonding interactions and ring electron densities in the optimized structures were further elucidated using Atoms in Molecules (AIM) analysis. The meta-Schiff base exhibited higher antimicrobial activity, particularly against E. coli, while the para-Schiff base showed a higher fluorescence quantum yield.
