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 In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

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 Mercury (element), Hgoxygen, O. It has a red or orange color. Mercury(II) oxide is a solid at room temperature and pressure. The mine ...

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 Classical qualitative inorganic analysis is a method of analytical chemistry which seeks to find the elemental composition of inorganic compounds. It is mainly focused on detecting ions in an aqueous solution, therefore materials in other forms may ...

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 grouping ...

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 req ...

: :C₆H₅OH + Hg(OAc)₂ → C₆H₄(OH)-2-HgOAc + HOAc The acetate group (OAc) that remains on mercury can be displaced by chloride: :C₆H₄(OH)-2-HgOAc + NaCl → C₆H₄(OH)-2-HgCl + NaOAc The Hg²⁺ 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 Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. I ...

and

alkoxide In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organic substituent. Alkoxides are strong bases and, whe ...

. 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 acry ...

with mercuric acetate in

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

gives an α-mercuri ester: :Hg(OAc)₂ + CH₂=CHCO₂CH₃ + CH₃OH → CH₃OCH₂CH(HgOAc)CO₂CH₃ + HOAc Exploiting the high affinity of mercury(II) for sulfur ligands, Hg(OAc)₂ can be used as a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

to deprotect thiol groups in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

. Similarly Hg(OAc)₂ has been used to convert

thiocarbonate Thiocarbonate describes a family of anions with the general chemical formula (''x'' = 0, 1, or 2): *for ''x'' = 2 it is monothiocarbonate ion *for ''x'' = 1 it is dithiocarbonate ion *for ''x'' = 0 it is trithiocarbonate ion Like the carbonate d ...

esters into dithiocarbonates: :(RS)₂C=S + H₂O + Hg(OAc)₂ → (RS)₂C=O + HgS + 2 HOAc Mercury(II) acetate is used for

oxymercuration The oxymercuration reaction is an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate (AcO–Hg–OAc) in aqueous solution to yield the addition of ...

reactions. A famous use of Hg(OAc)₂ was in the synthesis of

Idoxuridine Idoxuridine is an anti-herpesvirus antiviral drug. It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the iodine atom added to the uracil component blocks base pairing. I ...

References

{{Acetates Acetates Mercury(II) compounds