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New β-isatin aldehyde-N,N′-thiocarbohydrazones: preparation, spectroscopic studies and DFT approach to antioxidant characteristics

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Abstract

Five new Schiff bases of isatin and its derivatives were prepared from monothiocarbohydrazides and 5-chloro isatin. The chemical structures of the synthesized compounds were performed by 1H NMR, 13C NMR, and FT-IR spectroscopic techniques and elemental analysis. The in vitro antioxidant activities of all the products were determined by 1,1-Diphenyl-2-Picryl Hydrazyl free radical scavenging method. It also examined the antioxidant properties of the compounds based on quantum chemical calculations as well as supporting experimental spectroscopic data. Theoretical calculations carried out at B3LYP correlation functional with 6-311++g(2d,2p) basis set. Some chemical reactivity descriptors obtained from AIM, NCI, and ELF analysis were used to reveal the relationship between the electronic and antioxidant properties of the compounds. Furthermore, the bond lengths, charge densities, potential energy densities, inter-atomic dipole moments, and delocalization indices of the active phenolic hydrogen bonds of the compounds were shown to be parameters that can be used to determine the antioxidant properties of compounds.

Graphic Abstract

New β-isatin aldehyde-N,N′-thiocarbohydrazones were synthesized. Structures of synthesized molecules were clarified using spectroscopic methods. Antioxidant activities of the compounds were tested by the DPPH method. AIM, NCI, and ELF analysis were performed to investigate the relationship between the electronic properties and antioxidant activity.

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Authors and Affiliations

  1. Department of Mathematics and Science Education, Faculty of Education, Ondokuz Mayis University, Samsun, Turkey

    Hasan Yakan

  2. Department of Chemistry, Faculty of Art and Science, Kastamonu University, Kastamonu, Turkey

    Temel Kan Bakır & Halit Muğlu

  3. Biomedical Engineering Department, Faculty of Engineering and Architecture, Kastamonu University, Kastamonu, Turkey

    M. Serdar Çavuş

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  1. Hasan Yakan
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  2. Temel Kan Bakır
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  3. M. Serdar Çavuş
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  4. Halit Muğlu
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Contributions

HY was involved in synthesis, structure elucidation, and writing-original draft preparation. HM was involved in synthesis, methodology, and structure elucidation. TKB was involved in antioxidant activity studies and writing-original draft preparation. MSÇ was involved in density functional theory calculations and writing-original draft preparation.

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Correspondence to Hasan Yakan or M. Serdar Çavuş.

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Yakan, H., Bakır, T.K., Çavuş, M.S. et al. New β-isatin aldehyde-N,N′-thiocarbohydrazones: preparation, spectroscopic studies and DFT approach to antioxidant characteristics. Res Chem Intermed 46, 5417–5440 (2020). https://doi.org/10.1007/s11164-020-04270-0

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