Synthesis and characterization of 1:2 complex (4) of mercury(II) chloride with 1,3-dimethyl-1H-imidazole-2(3H)-thione (3) is discussed. Single crystal X-ray diffraction analysis showed the presence of strong intermolecular C–H···Cl hydrogen bonding between the Cl atoms of one molecular unit with the olefinic H atom and the H-atom of –NMe substituent of other molecular unit which lead to the formation chain-like structure. 1H NMR spectrum of 4 showed downfield shift of both olefinic and the methyl proton showing the presence of C–H···Cl hydrogen bonding and the formation of metal-thione complex. © 2016, The National Academy of Sciences, India.

Karri R.

Banerjee M.

Rai R.

Roy G.

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Shiv Nadar University

Proceedings of the National Academy of Sciences India Section A - Physical Sciences

Here we report the coordination behaviour of an imidazole-based [S 1 ]-donor ligand, 1,3-dimethyl-imidazole-2(3H)-thione (L1), and [S 2 ]-donor ligand, 3,3′-methylenebis(1-methyl-imidazole-2(3H)-thione) (L2) or 4,4′-(3,3′-methylenebis-(2-thioxo-2,3-dihydro-imidazole-3,1-diyl))dibutanoic acid (L3), with HgX 2 (X = Cl, Br or I) in solution and the solid state. NMR, UV-Vis spectroscopic, and single crystal X-ray studies demonstrated that L1 or L2 coordinated rapidly and reversibly to the mercury center of HgX 2 through the thione moiety. Treatment of L2 with HgCl 2 or HgBr 2 afforded 16-membered metallacycle k 1 -(L2) 2 Hg 2 Cl 4 or k 1 -(L2) 2 Hg 2 Br 4 where two Cl or Br atoms are located inside the ring. In contrast, treatment of L2 with HgI 2 afforded a chain-like structure of k 1 -[L2Hgl 2 ] n , possibly due to the large size of the iodine atom. Interestingly, [S 1 ] and [S 2 ]-donor ligands (L1, L2, and L3) showed an excellent efficacy to protect liver cells against HgCl 2 induced toxicity and the strength of their efficacy is in the order of L3 &gt; L2 &gt; L1. 30\% decrease of ROS production was observed when liver cells were co-treated with HgCl 2 and L1 in comparison to those cells treated with HgCl 2 only. In contrast, 45\% and 60\% decrease of ROS production was observed in the case of cells co-treated with HgCl 2 and thiones L2 and L3, respectively, indicating that [S 2 ]-donor ligands L2 and L3 have better cytoprotective effects against oxidative stress induced by HgCl 2 than [S 1 ]-donor ligand L1. Water-soluble ligand L3 with N-(CH 2 ) 3 CO 2 H substituents showed a better cytoprotective effect against HgCl 2 toxicity than L2 in liver cells. © 2019 The Royal Society of Chemistry.

Fulltext

Metallomics

Cytoprotective effects of imidazole-based [S 1 ] and [S 2 ]-donor ligands against mercury toxicity: A bioinorganic approach

Organomercurials including methylmercury are ubiquitous environmental pollutants and highly toxic to humans. Now it could be shown that N-methylimidazole based thiones/selones having an N-CH2CH2OH substituent are remarkably effective in detoxifying various organomercurials to produce less toxic HgE (E=S, Se) nanoparticles. Compounds lacking the N-CH2CH2OH substituent failed to produce HgE nanoparticles upon treatment with organomercurials, suggesting that this moiety plays a crucial role in the detoxification by facilitating the desulfurization and deselenization processes. This novel way of detoxifying organomercurials may lead to the discovery of new compounds to treat patients suffering from methylmercury poisoning. Getting rid of mercury: Insoluble HgE (E=S, Se) nanoparticles (NPs) are formed under physiologically relevant conditions when organomercurials are treated with N-methylimidazole-based thiones/selones having an N-CH2CH2OH substituent. Compounds lacking the N-CH2CH2OH substituent failed to produce HgE NPs upon treatment with organomercurials under identical reaction conditions. A novel pathway of detoxifying various organomercurials is described. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Angewandte Chemie - International Edition

Chemical Detoxification of Organomercurials

Dalton Transactions

Synthesis, characterization, DFT calculations, and electrochemical comparison of novel iron(ii) complexes with thione and selone ligands

Angewandte Chemie

Zeitschrift für Naturforschung B

Synthesis and Crystal Structures of New 1,3-Disubstituted Imidazoline-2-thiones

Journal of Environmental and Public Health

Mercury Toxicity and Treatment: A Review of the Literature

Synthesis and Characterization of 1:2 Complex of Mercury(II) Chloride with 1,3-Dimethyl-1H-Imidazole-2(3H)-Thione