Synthesis, Crystal structure, Electrochemical, Theoretical Studies and Antioxidant Activities of New Schiff Base

• Published in: Journal of molecular structure 2021-03, Vol.1227, p.129368, Article 129368
• Main Authors: MADI, Amira ABDELMADJID, HAFFAR, Djahida, BENGHANEM, Fatiha, GHEDJATI, Samira, TOUKAL, Linda, DORCET, Vincent, BOURZAMI, Riadh
• Format: Article
• Language: English
• Subjects: Antioxidant activity; Chemical Sciences; Cyclic voltammetry; DFT; Effective concentration; Schiff base; Synthesis
• ISSN: 0022-2860; 1872-8014; 0022-2860
• DOI: 10.1016/j.molstruc.2020.129368

•Synthesis of new Schiff base ligand.•Characterization of ligand by 1HNMR, 13CNMR, IR, UV-Vis.•Determination of the ligand's crystal structure by X-ray diffraction method.•Electrochemical studies.•Antioxidant activity studies of synthesized compound.•Theoretical studies using DFT calculations A novel Schiff base 2, 2′-((1E,1′E)-((4-methyl-1, 3-phenylene) bis (benzylidene)) bis (methylethylidene)) bis (4-methoxyphenol) (L) was the result of the reaction between 2, 4-diaminotoluene and 2-hydroxy-5-methoxy benzaldehyde. The compound (L) was characterized using IR, UV-Vis, 1H, and 13C NMR techniques. The structure of the ligand was determined by X-Ray Diffraction method (XRD). All experimental results were proved and explained theoretically exploiting DFT (Density Functional Theory) calculations. The electrochemical properties were studied through the cyclic voltammetry and the results were explained by the mean of the FMOs (Frontier Molecular Orbitals). The antioxidant activity of the synthesized Schiff base was evaluated by utilizing several tests as DPPH (1, 1-diphenyl-2-picryl hydrazyl), ABTS (2, 2′-azino-bis(3-ethyl benzthiazoline-6-sulfonicacid), hydroxyl radical scavenging test, reducing power test, β-carotene bleaching test as chemical methods, and the superoxide radical scavenging as electrochemical method. The effective concentration (EC50) showed that the compound has a good antioxidant activity, and the relationship between the structure-activity and the calculated electronic properties demonstrates that the compound has a good reactivity. [Display omitted]