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

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Sezgin B. , Tilki T. , Karabacak Atay Ç., Dede B.

Journal of Biomolecular Structure and Dynamics, 2020 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume:
  • Publication Date: 2020
  • Doi Number: 10.1080/07391102.2020.1863264
  • Title of Journal : Journal of Biomolecular Structure and Dynamics
  • Keywords: Antioxidant activity, azo, DPPH assay, bond dissociation enthalpy, density functional theory


© 2020 Informa UK Limited, trading as Taylor & Francis Group.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 1H-NMR, 13C-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 1H-NMR and 13C-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. Highlights Two pyridine derivative azo compounds were synthesized and evaluated for its antioxidant activity Molecular geometry and spectroscopic properties of the molecules were calculated in vitro and in silico antioxidant activities were investigated by DPPH free radical scavenging assay The PAB molecule showed better antioxidant activity than BHT Communicated by Ramaswamy H. Sarma.