The toxicological properties of mercury have been attributed to both its thiophilicity and its selenophilicity. Here we describe the reactivity of mercury compounds towards 1-methyl-1,3-dihydro-2H-benzimidazole-2-selone, H(sebenzimMe), a structural analogue of the selenoamino acid, selenoneine. These studies demonstrate that H(sebenzimMe) can cleave cleave a mercury-carbon bond. In addition, the phenylselenolate compound PhSeHgEt, undergoes facile protolytic cleavage of the Hg–C bond to release ethane at room temperature, whereas PhSeHgMe exhibits little reactivity under similar conditions. Interestingly, the cleavage of the Hg–C bond of PhSeHgEt is also more facile than that of the thiolate analogue, PhSHgEt, which demonstrates that coordination by selenium promotes protolytic cleavage of the mercury-carbon bond.

Mercury–selenium interactions and the protolytic cleavage of Hg–C bonds induced by 1-methyl-1,3-dihydro-2H-benzimidazole-2-selone

251st National Meeting (2016)

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