Mercury(II) acetate

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Mercury(II) acetate
Mercury(II)-acetate-from-xtal-1973-2D.png
Mercury(II)-acetate-from-xtal-1973-3D-balls-A.png
Mercury(II)-acetate-from-xtal-1973-3D-SF-A.png
Names
Other names
mercuric acetate
mercuriacetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.993
EC Number 209-766-2
RTECS number AI8575000
UNII
UN number 1629
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
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H300, H310, H330, H373, H400, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+233, P405, P501
NFPA 704
Flammability code 0: Will not burn. E.g., waterHealth code 4: Very short exposure could cause death or major residual injury. E.g., VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
4
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[edit]

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]

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[edit]

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[edit]

  1. ^ "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life and Health Concentrations (IDLH). 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