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Journal of the Serbian Chemical Society 2018 Volume 83, Issue 6, Pages: 707-721
https://doi.org/10.2298/JSC171001009Y
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DFT calculation, biological activity, anion sensing studies and crystal structure of (E)-4-chloro-2-((pyridin-2-ylimino)-methyl)phenol

Yildirim Nuray (Çanakkale Onsekiz Mart University, Health Services Vocational School, Çanakkale, Turkey)
Demir Neslihan (Çanakkale Onsekiz Mart University, Faculty of Arts and Sciences, Department of Biology, Çanakkale, Turkey)
Alpaslan Gökhan (Giresun University, Vocational School of Health Services, Department of Medical Services and Techniques, Giresun, Turkey)
Boyacioğlu Bahadir (Ankara University, Vocational School of Health Services, Keçioren-Ankara, Turkey)
Yildiz Mustafa (Çanakkale Onsekiz Mart University, Faculty of Arts and Sciences, Department of Chemistry, Çanakkale, Turkey)
Ünver Hüseyin (Ankara University, Faculty of Science, Department of Physics, Beşevler-Ankara, Turkey)

(E)-4-Chloro-2-[(pyridin-2-ylimino)methyl]phenol was synthesized in the reaction of 2-aminopyridine with 5-chlorosalicylaldehyde. The structure of compound was investigated by FTIR, UV–Vis, 1H-NMR, 13C-NMR and X-ray data. In addition, characterization of the compound was realized 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 were in good agreement with the structure predicted by the theoretical calculations using the density functional theory (DFT). Moreover, the antimicrobial activity of the compound was investigated against some bacteria and yeast cultures by the 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