Biological evaluation of a novel Schiff base ligand as an antioxidant agent: Synthesis, characterization and DFT computations of its Ni(II) and Cu(II) complexes

By condensation reaction in methanolic medium, a novel ligand using methoxy substituted amine and 5-bromosalicylaldehydic was synthesized. Then, its Cu- and Ni- complexes were also prepared under same experimental conditions. The final desired compounds, with high obtained yields, have been characterized and well discussed by EA-CHN, UV-Vis., FT-IR, NMR, SEM-EDX and MS spectrometry. The structure of the ligand was confirmed by X-ray crystallography showing an interesting intramolecular hydrogen bond and also intermolecular interactions (Br...CArom. and CH/it-type). The electronic properties were quantified by density functional theory (DFT) calculations using DFT- B3LYP/6-31 G (d,p) level basis set. The molecular structures, geometrical parameters, chemical reactivity, stability, molecular electrostatic potential (MEP) and Mulliken atomic charges were computed to identify the chemical reactive sites on the molecular surface. The antioxidant activities were studied theoretically involving various parameters such as bond dissociation enthalpy (BDE), ionization potentials (IPs), proton affinities (PA), proton dissociation enthalpy (PDE), electron transfer enthalpy (ETE) and radical stabilization energy (RSE). Experimentally, the antioxidant activities were also studied by using 2,2 '-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric ion reducing antioxidant power (FRAP) and nitric oxide scavenging (SNP) methods. The computational study of antioxidant activity is well correlated with their experimental results.