Two synthetic routes to bis(1-methyl-imidazole-2-thione)methane and bis(1-benzyl-imidazole-2-thione)methane complexes including sulfur atom insertion into copper−NHC bonds
| Autor: | Rosenildo Correa da Costa, Gareth R. Owen, Thomas Gray, Joshua Nunn, Mairi F. Haddow, Hazel A. Sparkes, Miriam Slivarichova, Ruua Ahmad |
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| Rok vydání: | 2017 |
| Předmět: |
Crystallography
010405 organic chemistry Ligand NHCs Organic Chemistry Inorganic chemistry Thiones chemistry.chemical_element Halide 010402 general chemistry 01 natural sciences Biochemistry Copper Sulfur Medicinal chemistry Methane 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Sulfur atom insertion chemistry Materials Chemistry Imidazole Physical and Theoretical Chemistry |
| Zdroj: | Slivarichova, M, Correa da Costa, R, Nunn, J, Ahmad, R, Haddow, M F, Sparkes, H A, Gray, T & Owen, G R 2017, ' Two synthetic routes to bis(1-methyl-imidazole-2-thione)methane and bis(1-benzyl-imidazole-2-thione)methane complexes including sulfur atom insertion into copper−NHC bonds ', Journal of Organometallic Chemistry . https://doi.org/10.1016/j.jorganchem.2017.05.015 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2017.05.015 |
| Popis: | The synthesis of novel bis-thione ligand, bis(1-benzyl-imidazole-2-thione)methane, SS Bn is reported for the first time. This ligand along with the previously reported bis(1-methyl-imidazole-2-thione)methane, SS Me has been utilised in the synthesis of a series of copper(I) halide complexes. The syntheses have been achieved by two methodologies. The first method involves the direct addition of the ligands to the copper halide salts, CuCl, CuBr and CuI. The second methodology involves an insertion of a sulfur atom into the copper‒NHC bond of the preformed organometallic complexes, [CuBr( CS Me )] 2 and [CuI( CS Me )] 2 {where CS Me = 1-(3-methyl-2H-imidazol-1-yl-2-thione)methyl-3-methyl-2H-imidazol-2-ylidene} and [CuBr( CS Bn )] 2 and [CuI( CS Bn )] 2 {where CS Bn = 1-(3-benzyl-2H-imidazol-1-yl-2-thione)methyl-3-benzyl-2H-imidazol-2-ylidene}. These sulfur atom insertion reactions provide an indirect route to the first copper−halide complexes containing the SS Me and SS Bn ligands. All six complexes prepared have been fully characterised by spectroscopic and analytical methods as well as X-ray crystallography. Dinuclear structures were obtained for the complexes containing SS Me , mononuclear complexes were obtained for the copper‒chloride and copper‒bromide complexes containing SS Bn and an extended network containing [Cu 4 I 4 ] clusters bridged by the SS Bn were formed for the corresponding copper‒iodide complex for the latter ligand. The coordination and structural features of the two bis-thione ligands are discussed. |
| Databáze: | OpenAIRE |
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