Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C–H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental (1)H and (13)C NMR studies on the key compound 2 are reported. The results of theoretical and experimental (1)H and (13)C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS(•+)) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC(50) = 4.30 ± 0.21 µM) and DPPH assay (IC(50) = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM.