Mercury(II) acetate

Mercury(II) acetate
Names
Other names
mercuric acetate
mercuriacetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.993
UNII
Properties
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 (354 °F; 452 K) (decomposes)
25 g/100 mL (10 °C)
100 g/100 mL (100 °C)
Solubility soluble in alcohol, diethyl ether
−100·10−6 cm3/mol
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
0
3
0
Lethal dose or concentration (LD, LC):
40.9 mg/kg (rat, oral)
23.9 mg/kg (mouse, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2]

Reactions

Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group that remains on mercury can be displaced by chloride:[3]

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:[4]

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

  1. ↑ "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Allmann, R. (1973). "Die Struktur des Quecksilber(II)-acetats". Z. Kristallogr. 138 (1–6): 366–373. doi:10.1524/zkri.1973.138.jg.366.
  3. ↑ 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
  4. ↑ 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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