Mercury(II) acetate
| Mercury(II) acetate | |
|---|---|
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| Other names mercuric acetate | |
| Identifiers | |
| CAS number | 1600-27-7  |
| PubChem | 15337 |
| ChemSpider | 14599 |
| UNII | R0G1MCT8Y5 |
| ChEBI | CHEBI:33211 |
| Jmol-3D images | {{#if:[Hg+2].[O-]C(=O)C.[O-]C(=O)C|Image 1 |
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| Properties | |
| Molecular formula | C4H6O4Hg |
| Molar mass | 318.678 g/mol |
| Appearance | white-yellow crystals |
| Odor | mild vinegar odor |
| Density | 3.28 g/cm³, solid |
| Melting point | 179 °C (decomposes) |
| Solubility in water | 25 g/100 mL (10 °C) 100 g/100 mL (100 °C) |
| Solubility | soluble in alcohol, diethyl ether |
| Hazards | |
| NFPA 704 |
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(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Mercury(II) acetate is the chemical compound with the formula Hg(O2CCH3)2. Commonly abbreviated Hg(OAc)2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors.
Structure
Mercury(II) acetate is a crystalline solid consisting of isolated Hg(OAc)2 molecules with Hg-O distances of 2.07 Å. Three long, weak intermolecular Hg···O bonds of about 2.75 Å are also present, resulting in a slightly distorted square pyramidal coordination geometry at Hg.[1]
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Reactions
Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group that remains on mercury can be displaced by chloride:[2]
- C6H5OH + Hg(OAc)2 → C6H4(OH)-2-HgOAc + HOAc
- C6H4(OH)-2-HgOAc + NaCl → C6H4(OH)-2-HgCl + NaOAc
The Hg2+ center binds to alkenes, inducing the addition of hydroxide and alkoxide. For example, treatment of methylacrylate with mercuric acetate in methanol gives an α-mercuri ester:[3]
- Hg(OAc)2 + CH2=CHCO2CH3 + CH3OH → CH3OCH2CH(HgOAc)CO2CH3 + HOAc
Mercury(II) has a high affinity for sulfur ligands. Hg(OAc)2 can be used as a reagent to remove the acetamidomethyl protecting group, which is used to "protect" thiol groups in organic synthesis. Similarly Hg(OAc)2 is a standard reagent to convert thiocarbonate esters into dithiocarbonates:
- (RS)2C=S + H2O + Hg(OAc)2 → (RS)2C=O + HgS + 2 HOAc
Mercury(II) acetate is used for oxymercuration reactions.
References
- ↑ R. Allmann (1973). Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem. 138: 366–373.
- ↑ Whitmore, F. C.; Hanson, E. R. "o-Chloromercuriphenol" Organic Syntheses, Collected Volume 1, p.161 (1941).http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0161
- ↑ Carter, H. E.; West, H. D. “dl-Serine” Organic Syntheses, Collected Volume 3, p.774 (1955). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV3P0774
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