Mercury(II) acetate

Mercury(II) acetate
Mercury(II) acetate
Identifiers
CAS number 1600-27-7 YesY
ChemSpider 14599 YesY
UNII R0G1MCT8Y5 YesY
ChEBI CHEBI:33211 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4H6O4Hg
Molar mass 318.70 g/mol
Appearance white crystals
Density 3.27 g/cm³, solid
Melting point

179°C (decomposes)

Solubility in water 25 g/100 mL (10°C)
Solubility soluble in alcohol
Hazards
NFPA 704
NFPA 704.svg
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3
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 YesY acetate (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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]

Ball-and-stick model of part of the crystal structure of mercury(II) acetate Space-filling model of part of the crystal structure of mercury(II) acetate

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

References

  1. ^ R. Allmann (1973). Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem. 138: 366–373. 
  2. ^ 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
  3. ^ 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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