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Experimental and theoretical study of S-benzyl β-N-(-2-methyl-3-phenylallylidene)dithiocarbazate as anti-bacterial agent

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Abstract

The NS based S-benzyl β-(N-2-methyl-3-phenylallylidene)dithiocarbazate (L) Schiff base was synthesized by 1:1 condensation method between S-benzyl dithiocarbazate and α-methyl-trans-cinnamaldehyde. The structure of the compound was elucidated by FT-IR, Mass, 13C-NMR, Raman, 1H-NMR, and UV–Vis both by spectroscopic and computational techniques. Its anti-bacterial activity is assayed against two commonly infection causing bacterial strains, namely gram-positive Staphylococcus aureus and gram-negative Escherichia coli. The results showed appreciable biological activity, and the activity increased with increase in concentration. Thermal stability of the ligand was carried by TGA up to 800 °C, and decomposes fully to give gaseous products. Theoretical investigation of (L) has been accomplished using the DFT-B3LYP quantum chemical method in combination with B3LYP exchange correlation functional. VEDA-4 (vibrational energy distribution analysis) software was employed for theoretical FT-IR spectrum analysis which yielded 114 fundamental vibrational modes along with a potential energy distribution percentage showing non-linearity of (L). Theoretically calculated parameters like UV–VIS, FT-IR, 1H-NMR, 13C-NMR, Raman, HOMO–LUMO energy gap and electrostatic potential were in conformity with calculated results.

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Acknowledgements

The author (Rayees A. Bhat) thanks the UGC (University Grant Commission), New Delhi for the monetary support provided (UGC-MANF Ref. No. MANF-2015-17-JAM-49814).

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  1. Centre of Research for Chemical Sciences, Government Model Science College, Jiwaji University, Gwalior, 474009, India

    Rayees A. Bhat & D. Kumar

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  1. Rayees A. Bhat
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Bhat, R.A., Kumar, D. Experimental and theoretical study of S-benzyl β-N-(-2-methyl-3-phenylallylidene)dithiocarbazate as anti-bacterial agent. Res Chem Intermed 45, 2565–2586 (2019). https://doi.org/10.1007/s11164-019-03752-0

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