Experimental and theoretical study of antioxidative properties of some salicylaldehyde and vanillic Schiff basesElectronic supplementary information (ESI) available: Characterization of compounds 1-10: bond lengths and angles, NBO charges and spin density, 1H NMR spectra, melting points. See DOI: 10.1039/c5ra02134k

• Main Authors: Petrovi, Zorica D, orovi, Jelena, Simijonovi, Dušica, Petrovi, Vladimir P, Markovi, Zoran
• Format: Article
• Language: English
• ISSN: 2046-2069
• DOI: 10.1039/c5ra02134k

The antioxidative capacity and structure-activity relationships of ten Schiff bases were investigated experimentally and theoretically. All compounds contain the aniline moiety, while the aldehyde part is either salicylaldehyde or vanillin. The DPPH assay was used to test the potential antioxidative activity of these compounds, and DFT study was used to investigate their electronic structures and provide insight into their structure-activity relationships. The effect of the position of the hydroxy, as well other groups present, on the antioxidative activity was examined. The possible radical scavenging mechanism was determined in polar (water and methanol), and nonpolar (benzene) solvents. Based on the experimental and computational results, compounds 7 and 8 exhibit the highest radical scavenging properties. A set of ten phenolic Schiff bases was evaluated for their antioxidative properties. Two of them, one salicylaldehyde and one vanillic, showed high activity. Parameters obtained by DFT supported the experimental findings.