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Organomercury chemistry
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Many organomercury compounds are highly toxic, but some are used in medicine, e.g., merbromin ("Mercurochrome") and the vaccine preservative thiomersal.
Most organomercury compounds feature diamagnetic Hg(II) and adopt a linear C-Hg-X structure.[citation needed] Indeed, no organic derivatives of Hg2+
2 are known, as Hg2+
2 requires electronegative subtituents for condensed-phase stability.
Hg(II) derivatives are neither Lewis basic or Lewis acidic. They are stable to oxygen and water, indicating the low polarity of the Hg-C bond.
Mercury forms a compound with two cyclopentadiene ligands, but the resulting complex may not be a metallocene. When made in the 1950s, it was too sensitive for structural determination.
The toxicity of organomercury compounds presents both dangers and benefits. Dimethylmercury in particular is notoriously toxic, but found use as an antifungal agent and insecticide. Merbromin and phenylmercuric borate are used as topical antiseptics, while thimerosal is safely used as a preservative for vaccines and antitoxins.
Reflecting the strength of the C-Hg bond, organomercury compounds are generated by many methods. Indeed, mercury adsorbs onto laboratory glassware, such that laboratories performing mercury experiments may have difficulty avoiding C–Hg bond formation.
In some regards, organomercury chemistry more closely resembles organopalladium chemistry and contrasts with organocadmium compounds.
Metallic Hg reacts only slowly with methyl iodide to give dimethylmercury. With more electrophilic alkylating agents, the reaction is more efficient. Also, sodium amalgam react with organic halides to give diorganomercury compounds.
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Organomercury chemistry
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Many organomercury compounds are highly toxic, but some are used in medicine, e.g., merbromin ("Mercurochrome") and the vaccine preservative thiomersal.
Most organomercury compounds feature diamagnetic Hg(II) and adopt a linear C-Hg-X structure.[citation needed] Indeed, no organic derivatives of Hg2+
2 are known, as Hg2+
2 requires electronegative subtituents for condensed-phase stability.
Hg(II) derivatives are neither Lewis basic or Lewis acidic. They are stable to oxygen and water, indicating the low polarity of the Hg-C bond.
Mercury forms a compound with two cyclopentadiene ligands, but the resulting complex may not be a metallocene. When made in the 1950s, it was too sensitive for structural determination.
The toxicity of organomercury compounds presents both dangers and benefits. Dimethylmercury in particular is notoriously toxic, but found use as an antifungal agent and insecticide. Merbromin and phenylmercuric borate are used as topical antiseptics, while thimerosal is safely used as a preservative for vaccines and antitoxins.
Reflecting the strength of the C-Hg bond, organomercury compounds are generated by many methods. Indeed, mercury adsorbs onto laboratory glassware, such that laboratories performing mercury experiments may have difficulty avoiding C–Hg bond formation.
In some regards, organomercury chemistry more closely resembles organopalladium chemistry and contrasts with organocadmium compounds.
Metallic Hg reacts only slowly with methyl iodide to give dimethylmercury. With more electrophilic alkylating agents, the reaction is more efficient. Also, sodium amalgam react with organic halides to give diorganomercury compounds.