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Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity

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Abstract

A series of novel thiosemicarbazones including Schiff bases were synthesized by treatment of various aryl-substituted aldehydes with thiosemicarbazides in ethanol containing one drop of hydrochloric acid at reflux for 3–5 h. For this, thiosemicarbazides were obtained from hydrazine monohydrate and isothiocyanates in cold dry ethanol at 0 °C for 1 h. FT-IR, 1H NMR, 13C NMR, and LC–MS/MS spectroscopic methods and elemental analysis were used to characterize the identification of the synthesized products. The in vitro antioxidant activity of these compounds was tested by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical trapping method. All of the synthesized compounds showed lower antioxidant activity than the ascorbic acid standard and followed the sequence I > VII > X > VI > IV > IX > XI > II > V > III > VIII.

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Acknowledgements

I would like to thank the Scientific Technological Research and Applications Center (Gübitam) and Dr. Ömer Faruk Ensari for taking the NMR spectra.

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

    Hasan Yakan

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  1. Hasan Yakan
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Yakan, H. Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity. Res Chem Intermed 46, 3979–3995 (2020). https://doi.org/10.1007/s11164-020-04185-w

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