Synthesis, Characterization, Single crystal investigation, Hirshfeld surface analysis and Antibacterial Evaluation of New Dithiophosphonate Compounds

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Document Type : Research Article

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Department of Chemistry, Germi Branch, Islamic Azad University, Germi, Iran

Abstract

The reaction of Lawesson’s reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, LR) with hexamethyleneimine (Azepane), morpholine and diisobutylamine in wet toluene produced [(p-C6H4OMe)2(O)(PS2-)2(C6H12NH2+)2] (I), [(p-C6H4OMe)2(O)(PS2-)2(OC4H8NH2+)2] (II), [(p-C6H4OMe)2(O)(PS2-)2(C8H18NH2+)2] (III), respectively. Compounds I, II and III are characterized by IR spectroscopy, elemental analysis, 1H, 13C and 31P NMR techniques. The reaction of compounds with LR produced ion pair. The X-ray crystallography studies of compound I showed that its asymmetric unit is composed of two independent molecules. In this compound, the P atom is in a tetrahedral environment. Also, the crystal structure of the compound I revealed that the P(S)…H–N hydrogen bonds caused the formation of a one-dimensional arrangement. 3D Hirshfeld surfaces (HS) and 2D fingerprint plots (FPs) were used to analyze intramolecular interactions in compound I. The results of analysis of HS and FPs of compound I demonstrated that H…H interactions had the highest proportions. Antibacterial potential of these compounds were tested against four bacteria, namely Pseudomonas aeruginosa (G-), Escherichia coli (G-), Micrococcus luteus (G+) and Bacillus subtilis (G+).

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Iranian Journal of Chemistry and Chemical Engineering

Articles in Press, Accepted Manuscript
Available Online from 20 September 2023

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