Mercury(II) acetate is the
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the
formula Hg(
O2 CC
H3)
2. Commonly abbreviated Hg(OAc)
2, this compound is employed as a reagent to generate
organomercury
Organomercury refers to the group of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ...
compounds from unsaturated organic precursors. It is a white water-soluble solid, but samples appear yellowish with time owing to decomposition.
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.
Synthesis and reactions
Mercury(II) acetate can be produced by reaction of
mercuric oxide
Mercury(II) oxide, also called mercuric oxide or simply mercury oxide, is the inorganic compound with the formula Hg O. It has a red or orange color. Mercury(II) oxide is a solid at room temperature and pressure. The mineral form montroydite is v ...
with acetic acid.
Inorganic reactions
Mercury(II) acetate in acetic acid solution reacts with
H2S to rapidly precipitate the black (β)
polymorph of
HgS. With gentle heating of the slurry, the black solid converts to the red form. The mineral cinnabar is red HgS. The precipitation of HgS as well as a few other sulfides, using hydrogen sulfide is a step in
qualitative inorganic analysis.
Organic chemistry
Electron-rich
arene
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...
s undergo "mercuration" upon treatment with Hg(OAc)
2. This behavior is illustrated with
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...
:
:C
6H
5OH + Hg(OAc)
2 → C
6H
4(OH)-2-HgOAc + HOAc
The acetate group (OAc) that remains on mercury can be displaced by chloride:
:C
6H
4(OH)-2-HgOAc + NaCl → C
6H
4(OH)-2-HgCl + NaOAc
The Hg
2+ center binds to
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s, inducing the addition of
hydroxide and
alkoxide. For example, treatment of methyl
acrylate
Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion C H2=CHC OO−. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acr ...
with mercuric acetate in
methanol gives an α-mercuri ester:
:Hg(OAc)
2 + CH
2=CHCO
2CH
3 +
CH3OH → CH
3OCH
2CH(HgOAc)CO
2CH
3 + HOAc
Exploiting the high affinity of mercury(II) for sulfur ligands, Hg(OAc)
2 can be used as a
reagent to
deprotect thiol groups in
organic synthesis. Similarly Hg(OAc)
2 has been used to convert
thiocarbonate esters into dithiocarbonates:
:(RS)
2C=S + H
2O + Hg(OAc)
2 → (RS)
2C=O +
HgS + 2 HOAc
Mercury(II) acetate is used for
oxymercuration reactions.
A famous use of Hg(OAc)
2 was in the synthesis of
Idoxuridine.
References
{{Acetates
Acetates
Mercury(II) compounds