Faculty of Science & Art, Department of Chemistry, Süleyman Demirel University, Isparta, Turkey.
Faculty of Education, Department of Basic Education, Burdur Mehmet Akif Ersoy University, Burdur, Turkey.
J Biomol Struct Dyn. 2022 Jul;40(11):4921-4932. doi: 10.1080/07391102.2020.1863264. Epub 2020 Dec 24.
Two azo compounds 2-(3-pyridylazo)-3,5-dihydroxybenzoic acid () and 4-(3-pyridylazo)resorcinol () thought to have the potential to be used as antioxidants were designed, synthesized and antioxidant activities were investigated both and . The synthesized compounds were characterized by H-NMR, C-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-NMR and C-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 and were investigated by using DPPH assay. It was determined that the molecule showed better antioxidant activity than 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. HighlightsTwo pyridine derivative azo compounds were synthesized and evaluated for its antioxidant activityMolecular geometry and spectroscopic properties of the molecules were calculated and antioxidant activities were investigated by DPPH free radical scavenging assayThe PAB molecule showed better antioxidant activity than BHTCommunicated by Ramaswamy H. Sarma.
两种偶氮化合物 2-(3-吡啶偶氮)-3,5-二羟基苯甲酸()和 4-(3-吡啶偶氮)间苯二酚()被认为具有作为抗氧化剂的潜力，被设计、合成并研究了它们的抗氧化活性。合成的化合物通过 H-NMR、C-NMR、FT-IR、UV-Vis 和质谱进行了表征。在基态下，通过密度泛函理论(DFT)，使用 B3LYP 水平和 6-311G(d,p)基组，对合成化合物的分子几何形状和振动频率进行了计算。采用无规坐标原子轨道(GIAO)方法确定了 H-NMR 和 C-NMR 的化学位移值。通过含时密度泛函理论(TD-DFT)方法进行 HOMO-LUMO 计算。合成化合物的计算光谱数据与实验数据完全吻合。通过 DPPH 测定法研究了和的抗氧化活性。结果表明，分子显示出比和更好的抗氧化活性，而作为标准抗氧化剂的丁基羟基甲苯(BHT)。此外，借助 DFT 计算得到的热力学稳定性参数与 DPPH 测定法得出的抗氧化能力顺序相当吻合。
