DFT calculation, biological activity, anion sensing studies and crystal structure of (E)-4-chloro-2-((pyridin-2-ylimino)-methyl)phenol

Nuray Yildirim, Neslihan Demir, Gökhan Alpaslan, Bahadir Boyacioglu, Mustafa Yildiz, Huseyin Ünver

Abstract


(E)-4-chloro-2-((pyridin-3-ylimino)methyl)phenol was synthesized from the reaction of 2-aminopyridine with 5-chlorosalicylaldehyde. The structure of compound has been investigated by FTIR, UV-VIS, 1H-NMR, 13C-NMR and X-ray data. Also, characterization of the compound was carried out using theoretical quantum-mechanical calculations and experimental spectroscopic methods. The molecular structure of the compound was confirmed using X-ray single-crystal data, NMR, FTIR and UV-VIS, which was in good agreement with the structure predicted by the theoretical calculations using density functional theory (DFT). Moreover, the antimicrobial activity of the compound was investigated against some bacteria and yeast cultures by broth microdilution test. UV-Vis spectroscopy studies of the interactions between the Schiff base and calf thymus DNA (CT-DNA) showed that the compound interacts with CT-DNA via electrostatic binding.  The colorimetric response of the compound receptors was investigated before and after the addition of an equivalent amount of each anion to evaluate anion recognition properties.

Keywords


UV-Vis spectroscopy; 2-aminopyridine; anti-microbial activity; DNA binding; X-ray crystallography

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DOI: https://doi.org/10.2298/JSC171001009Y

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