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Comparative in vitro and DFT antioxidant studies of phenolic group substituted pyridine-based azo derivatives

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dc.creator Tilki, Tahir
dc.creator Karabacak Atay, Çiğdem
dc.creator Dede, Bülent
dc.creator Sezgin, Barış
dc.date 2022-06-01T00:00:00Z
dc.identifier 4aa88413-f448-46ae-9890-e11774822249
dc.identifier 10.1080/07391102.2020.1863264
dc.identifier https://avesis.sdu.edu.tr/publication/details/4aa88413-f448-46ae-9890-e11774822249/oai
dc.description Two azo compounds 2-(3-pyridylazo)-3,5-dihydroxybenzoic acid (PAB) and 4-(3-pyridylazo)resorcinol (PAR) thought to have the potential to be used as antioxidants were designed, synthesized and antioxidant activities were investigated both in vitro and in silico. The synthesized compounds were characterized by H-1-NMR, C-13-NMR, FT-IR, UV-Vis and mass spectra. The molecular geometry and vibrational frequency calculations of the synthesized compounds in ground state were performed by the density functional theory (DFT) employing B3LYP level with the 6-311 G(d,p) basis set. The gauge independent atomic orbital (GIAO) method was used to determine the chemical shift values of H-1-NMR and C-13-NMR. HOMO-LUMO calculations were carried out by time-dependent DFT (TD-DFT) approach. Computational spectroscopic data of the synthesized compounds are fully compatible with experimental ones. The antioxidant activities of the PAB and PAR were investigated by using DPPH assay. It was determined that the PAB molecule showed better antioxidant activity than PAR and, butylated hydroxytoluene (BHT) which is the standard antioxidant. In addition, the thermodynamic stability parameters obtained with the help of DFT calculations were found to be quite compatible with the antioxidant capacity sequence derived from the DPPH assay.
dc.language eng
dc.rights info:eu-repo/semantics/closedAccess
dc.title Comparative in vitro and DFT antioxidant studies of phenolic group substituted pyridine-based azo derivatives
dc.type info:eu-repo/semantics/article


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