Silver acetate is a

coordination compound A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

with the empirical formula CH₃CO₂Ag (or AgC₂H₃O₂). A

photosensitive Photosensitivity is the amount to which an object reacts upon receiving photons, especially visible light. In medicine, the term is principally used for abnormal reactions of the skin, and two types are distinguished, photoallergy and phototoxicity. ...

, white, crystalline solid, it is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion.

Synthesis and structure

Silver acetate can be synthesized by the reaction of

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

and

silver carbonate Silver carbonate is the chemical compound with the formula Ag2 C O3. This salt is yellow but typical samples are grayish due to the presence of elemental silver. It is poorly soluble in water, like most transition metal carbonates. Preparation a ...

. :2 CH₃CO₂H + Ag₂CO₃ → 2 AgO₂CCH₃ + H₂O + CO₂ Solid silver acetate precipitates upon concentration of solutions of

silver nitrate Silver nitrate is an inorganic compound with chemical formula . It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called ''lunar causti ...

and

sodium acetate Sodium acetate, CH3COONa, also abbreviated Sodium, NaOxygen, OAcetyl, Ac, is the sodium Salt (chemistry), salt of acetic acid. This salt is colorless, deliquescent, and hygroscopy, hygroscopic. Applications Biotechnological Sodium acetate is u ...

. The structure of silver acetate consists of 8-membered Ag₂O₄C₂ rings formed by a pair of acetate ligands bridging a pair of silver centres.

Reactions

Silver acetate finds use in certain transformations in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

Sulfenamide synthesis

Silver acetate is used to prepare sulfenamides from

disulfide In chemistry, a disulfide (or disulphide in British English) is a compound containing a functional group or the anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups. In inorg ...

s and

secondary amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s: : R₂NH + AgOAc + (RS)₂ → R₂NSR + AgSR + HOAc

Hydrogenation

A solution of silver acetate in pyridine absorbs hydrogen, producing metallic

silver Silver is a chemical element; it has Symbol (chemistry), symbol Ag () and atomic number 47. A soft, whitish-gray, lustrous transition metal, it exhibits the highest electrical conductivity, thermal conductivity, and reflectivity of any metal. ...

: :2 CH₃CO₂Ag + H₂ → 2 Ag + 2 CH₃CO₂H

Direct ''ortho''-arylation

Silver acetate is a reagent for direct ''ortho''-arylation (to install two adjacent substituents on an aromatic ring) of benzylamines and N-methylbenzylamines. The reaction is palladium-catalyzed and requires a slight excess of silver acetate. This reaction is shorter than previous ''ortho''-arylation methods.

Oxidative dehalogenation

Silver acetate can be used to convert certain

organohalogen Halocarbon compounds are chemical compounds in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms (fluorine, chlorine, bromine or iodine – ) resulting in the formation of organofluorine compounds, orga ...

compounds into

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

s. It may be used, in spite of its high cost, in instances where a mild and selective reagent is desired.

Woodward cis-hydroxylation

Silver acetate in combination with

iodine Iodine is a chemical element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at , and boils to a vi ...

forms the basis of the Woodward cis-hydroxylation. This reaction selectively converts an

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

into a cis-

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...

Uses

In the health field, silver acetate-containing products have been used in gum, spray, and lozenges to deter smokers from smoking. The silver in these products, when mixed with smoke, creates an unpleasant metallic taste, thus deterring them from smoking. Lozenges containing 2.5 mg of silver acetate showed "modest efficacy" on 500 adult smokers tested over a three-month period. However, over a period of 12 months, prevention failed. In 1974, silver acetate was first introduced in Europe as an over-the-counter smoking-deterrent lozenge (Repaton) and then three years later as a chewing gum (Tabmint). Silver acetate is also a well known precursor used in printed electronics. Particularly, complexes of silver acetate have been reported to form particle free "reactive inks" that form traces that approach bulk silver conductivity (within one order of magnitude).

Safety

The LD₅₀ of silver acetate in mice is 36.7 mg/kg. Low doses of silver acetate in mice produced hyper-excitability,

ataxia Ataxia (from Greek α- negative prefix+ -τάξις rder= "lack of order") is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in e ...

, central nervous system depression, labored breathing, and even death. The U.S. FDA recommends that silver acetate intake be limited to 756 mg over a short period of time; excessive intake may cause

argyria Argyria or argyrosis is a condition caused by excessive exposure to chemical compounds of the element silver, or silver dust. The most dramatic symptom of argyria is that the skin turns blue or blue-gray, and is usually most prominent in sun-ex ...