Dimethylmercury

Dimethylmercury ((CH3)2Hg), also known as mercury dimethanide, is an extremely toxic organomercury compound. A highly volatile, reactive, flammable, and colorless liquid, dimethylmercury is one of the strongest known neurotoxins, with a quantity of less than 0.1 mL capable of inducing severe mercury poisoning resulting in death, and is easily absorbed through the skin. Dimethylmercury is capable of permeating many materials, including plastic and rubber compounds. It has been described as having a slightly sweet odor, although those who have reported its smell were exposed to harmful amounts. The compound was one of the earliest organometallics reported, reflecting its considerable stability. The compound was first prepared by George Buckton in 1857 by a reaction of methylmercury iodide with potassium cyanide: 2 CH3HgI + 2 KCN → Hg(CH3)2 + 2 KI + (CN)2 + Hg Later, Frankland discovered that it could be synthesized by treating sodium amalgam with methyl halides: Hg + 2 Na + 2 CH3I → Hg(CH3)2 + 2 NaI It can also be obtained by alkylation of mercuric chloride with methyllithium: HgCl2 + 2 LiCH3 → Hg(CH3)2 + 2 LiCl The molecule adopts a linear structure with Hg–C bond lengths of 2.083 Å. An unusual feature of this compound is its low reactivity towards proton sources, being stable in water and reacting with mineral acids at a significant rate only at elevated temperatures, whereas the corresponding organocadmium and organozinc compounds (and most metal alkyls in general) hydrolyze rapidly. The difference reflects the high electronegativity of Hg (Pauling EN = 2.00) and the low affinity of Hg(II) for oxygen ligands. The compound undergoes a redistribution reaction with mercuric chloride to give methylmercury chloride: (CH3)2Hg + HgCl2 → 2 CH3HgCl Whereas dimethylmercury is a volatile liquid, methylmercury chloride is a crystalline solid. Dimethylmercury currently has few applications because of the risks involved.

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Methylmercury

Methylmercury (sometimes methyl mercury) is an organometallic cation with the formula [CH3Hg]+. It is the simplest organomercury compound. Methylmercury is extremely toxic, and its derivatives are the major source of organic mercury for humans. It is a bioaccumulative environmental toxicant. "Methylmercury" is a shorthand for the hypothetical "methylmercury cation", sometimes written methylmercury(1+) cation or methylmercury(II) cation. This functional group is composed of a methyl group bonded to an atom of mercury.

Dimethylmercury

Organomercury chemistry

Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs. The toxicity of organomercury compounds presents both dangers and benefits.

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