title: Protolytic cleavage of Hg-C bonds induced by 1-methyl-1,3-dihydro-2H-benzimidazole-2-selone: synthesis and structural characterization of mercury complexes.
abstract: Multinuclear ((1)H, (77)Se, and (199)Hg) NMR spectroscopy demonstrates that 1-methyl-1,3-dihydro-2H-benzimidazole-2-selone, H(sebenzim(Me)), a structural analogue of the selenoamino acid, selenoneine, binds rapidly and reversibly to the mercury centers of HgX2 (X = Cl, Br, I), while X-ray diffraction studies provide evidence for the existence of adducts of composition [H(sebenzim(Me))]xHgX2 (X = Cl, x = 2, 3, 4; X = I, x = 2) in the solid state. H(sebenzim(Me)) also reacts with methylmercury halides, but the reaction is accompanied by elimination of methane resulting from protolytic cleavage of the Hg-C bond, an observation that is of relevance to the report that selenoneine demethylates CysHgMe, thereby providing a mechanism for mercury detoxification. Interestingly, the structures of [H(sebenzim(Me))]xHgX2 exhibit a variety of different hydrogen bonding patterns resulting from the ability of the N-H groups to form hydrogen bonds with chlorine, iodine, and selenium.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, United States.
authors.forename: Joshua H
authors.initials: JH
authors.lastname: Palmer
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, United States.
authors.forename: Gerard
authors.initials: G
authors.lastname: Parkin
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D008628:Mercury / Q000737:chemistry*; D008767:Methylmercury Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D010782:Photolysis; D012643:Selenium / Q000737:chemistry*
chemical_list: D001562:Benzimidazoles; D008767:Methylmercury Compounds; D016566:Organoselenium Compounds; D002244:Carbon; C031000:benzimidazole; D008628:Mercury; D012643:Selenium
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