Synthesis, characterization, quantum chemical calculations and antioxidant activity of new bis-isatin carbohydrazone and thiocarbohydrazone derivatives

Publication date: Available online 4 July 2019Source: Journal of Molecular StructureAuthor(s): Halit Muğlu, M. Serdar Çavuş, Temelkan Bakır, Hasan YakanAbstract1,5-Bis(5-chloro-2-oxoindolin-3-ylidene)thiocarbohydrazone (3), 1,5-Bis(5-metoxy-2-oxoindolin-3-ylidene)thiocarbohydrazone (4), 1,5-Bis(5-metoxy-2-oxoindolin-3-ylidene)carbohydrazone (5) were obtained from isatins and thio/carbohydrazides under reflux in absolute ethanol. The structures of these synthesized compounds were determined using FT-IR, 1H NMR, 13C NMR spectroscopy, and elemental analysis. Quantum chemical calculations were also performed at B3LYP/6-311++G(2d,2p) level in order to obtain information about the molecular geometries and electronic data, such as HOMO-LUMO energy eigenvalues and density of states (DOSs). In addition, structural and antioxidant properties of the compounds were studied theoretically. QTAIM analysis was performed to investigate the relationship between intramolecular interactions, electronic data and antioxidant activity. The in vitro antioxidant activity of all the compounds was determined by 1,1-Diphenyl-2-Picryl Hydrazyl (DPPH) free radical scavenging method. Antioxidant activity was followed by Ascorbic acid> 3 > 4> 5.Graphical abstractNew bis-isatin carbohydrazone and thiocarbohydrazone derivatives were synthesized. The structures were determined using FT-IR, 1H NMR, 13C NMR spectroscopy, and elemental analysis spectroscopic methods. The synthesized compoun...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research

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