Multinuclear
(1H, 77Se, and 199Hg) NMR spectroscopy
demonstrates that 1-methyl-1,3-dihydro-2H-benzimidazole-2-selone,
H(sebenzimMe), 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(sebenzimMe)]xHgX2 (X = Cl, x = 2, 3, 4; X = I, x = 2) in the solid
state. H(sebenzimMe) 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(sebenzimMe)]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.