Zinc(II)-methimazole complexes: synthesis and reactivity

Isaia Francesco; Aragoni Maria Carla; Arca Massimiliano; Bettoschi Alexandre; Caltagirone Claudia; Castellano Carlo; Demartin Francesco; Lippolis Vito; Pivetta Tiziana; Valletta Elisa

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Zinc(II)-methimazole complexes: synthesis and reactivity

机译：锌（II）-甲基咪唑配合物：合成与反应性

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The tetrahedral S-coordinated complex [Zn(MeImHS)(4)](ClO4)(2), synthesised from the reaction of [Zn(ClO4)(2)] with methimazole (1-methyl-3H-imidazole-2-thione, MeImHS), reacts with triethylamine to yield the homoleptic complex [Zn(MeImS)(2)] (MeImS = anion methimazole). ESI-MS and MAS C-13-NMR experiments supported MeImS acting as a (N, S)-chelating ligand. The DFT-optimised structure of [Zn(MeImS)(2)] is also reported and the main bond lengths compared to those of related Zn-methimazole complexes. The complex [Zn(MeImS)(2)] reacts under mild conditions with methyl iodide and separates the novel complex [Zn(MeImSMe)(2)I-2] (MeImSMe = S-methylmethimazole). X-ray diffraction analysis of the complex shows a ZnI2N2 core, with the methyl thioethers uncoordinated to zinc. Conversely, the reaction of [Zn( MeImS)(2)] with hydroiodic acid led to the formation of the complex [Zn(MeImHS)(2)I-2] having a ZnI2S2 core with the neutral methimazole units S-coordinating the metal centre. The Zn-coordinated methimazole can markedly modify the coordination environment when changing from its thione to thionate form and vice versa. The study of the interaction of the drug methimazole with the complex [Zn(MeIm)(4)](2+) (MeIm = 1-methylimidazole) - as a model for Zn-enzymes containing a N-4 donor set from histidine residues shows that methimazole displaces only one of the coordinated MeIm molecules; the formation constant of the mixed complex [Zn(MeIm)(3)(MeImHS)](2+) was determined.

机译：四面体S配位配合物[Zn（MeImHS）（4）]（ClO4）（2），是由[Zn（ClO4）（2）]与异丁唑（1-甲基-3H-咪唑-2-硫酮）反应合成的，MeImHS）与三乙胺反应生成均化络合物[Zn（MeImS）（2）]（MeImS =阴离子甲巯咪唑）。 ESI-MS和MAS C-13-NMR实验支持MeImS充当（N，S）螯合配体。 DFT优化的[Zn（MeImS）（2）]结构也有报道，并且与相关的Zn-甲基咪唑配合物相比，其主要键长也有所不同。络合物[Zn（MeImS）（2）]在温和条件下与碘甲烷反应，并分离出新型络合物[Zn（MeImSMe）（2）I-2]（MeImSMe = S-甲基甲基咪唑）。配合物的X射线衍射分析显示出ZnI 2 N 2核，其中甲基硫醚与锌不配位。相反，[Zn（MeImS）（2）]与氢碘酸的反应导致形成了具有ZnI2S2核和中性甲硫唑单元S配位的金属的配合物[Zn（MeImHS）（2）I-2]。中央。从其硫酮形式转变为硫氰酸盐形式时，锌配位的甲巯咪唑可以显着改变配位环境，反之亦然。甲巯咪唑与复合物[Zn（MeIm）（4）]（2+）（MeIm = 1-甲基咪唑）相互作用的研究-作为含组氨酸残基的含N-4供体的锌酶模型表明甲巯咪唑仅取代一种配位的MeIm分子;确定混合配合物[Zn（MeIm）（3）（MeImHS）]（2+）的形成常数。

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《Dalton transactions: An international journal of inorganic chemistry》 |2015年第21期|共10页
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Isaia Francesco; Aragoni Maria Carla; Arca Massimiliano; Bettoschi Alexandre; Caltagirone Claudia; Castellano Carlo; Demartin Francesco; Lippolis Vito; Pivetta Tiziana; Valletta Elisa;
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机译：锌（II）-甲基咪唑配合物：合成与反应性
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Zinc(II)-methimazole complexes: synthesis and reactivity

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