Silver acetate

{{chembox

|Watchedfields = changed

|verifiedrevid = 477003493

|Name = Silver acetate

|ImageFile = Ag2(OAc)2.png

|ImageSize = 120px

|ImageFile2 = Silver acetate.jpg

|ImageName = Silver acetate

|OtherNames = Acetic acid, silver(I) salt
Silver ethanoate
Argentous acetate
Argentous ethanoate

|IUPACName = Silver(I) acetate

|SystematicName = Silver(I) ethanoate

|Section1 = {{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 10772

|PubChem = 11246

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 19PPS85F9H

|InChI = 1/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1

|InChIKey = CQLFBEKRDQMJLZ-REWHXWOFAJ

|SMILES = CC(=O)[O-].[Ag+]

|SMILES_Comment = ionic monomer

|SMILES1 = C[C-]0O[Ag+]O[C-](C)O[Ag]O0

|SMILES1_Comment = coordination dimer without Ag-Ag bond

|SMILES2 = C[C-]0O[Ag+]1O[C-](C)O[Ag]1O0

|SMILES2_Comment = coordination dimer with Ag-Ag bond

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = CQLFBEKRDQMJLZ-UHFFFAOYSA-M

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 563-63-3

|EINECS = 209-254-9

|RTECS = AJ4100000

}}

|Section2 = {{Chembox Properties

|Formula = AgC₂H₃O₂

|MolarMass = 166.912 g/mol

|Appearance = white to slightly grayish powder
slightly acidic odor

|Density = 3.26 g/cm³, solid

|Solubility = 1.02 g/100 mL(20 °C)

|MeltingPtC = 220

|MeltingPt_notes = (decomposes)

|SolubilityProduct = 1.94{{e|−3}}{{cite book |author1=John Rumble |title=CRC Handbook of Chemistry and Physics |date=June 18, 2018 |publisher=CRC Press |isbn=978-1138561632 |pages=5–189|edition=99 |language=English}}

|MagSus = −60.4·10⁻⁶ cm³/mol

}}

|Section3 = {{Chembox Hazards

|GHS_ref={{cite web |title=Silver acetate |url=https://pubchem.ncbi.nlm.nih.gov/compound/11246#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=15 December 2021 |language=en}}

|GHSPictograms = {{GHS07}}{{GHS09}}

|GHSSignalWord = Warning

|HPhrases = {{H-phrases|315|319|335|400}}

|PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|391|403+233|405|501}}

|NFPA-H = 1 | NFPA-F = 0 | NFPA-R = 0}}

}}

Silver acetate is a coordination compound with the empirical formula CH₃CO₂Ag (or AgC₂H₃O₂). A photosensitive, 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 and silver carbonate.{{cite journal|last=Logvinenko|first=V.|author2=Polunina, O. |author3=Mikhailov, Yu |author4=Mikhailov, K. |author5= Bokhonov, B. |title=Study of Thermal Decomposition of Silver Acetate|journal=Journal of Thermal Analysis and Calorimetry|year=2007|volume=90|issue=3|pages=813–816|doi=10.1007/s10973-006-7883-9|s2cid=96769867}}

:2 CH₃CO₂H + Ag₂CO₃ → 2 AgO₂CCH₃ + H₂O + CO₂

Solid silver acetate precipitates upon concentration of solutions of silver nitrate and sodium acetate.

The structure of silver acetate consists of 8-membered Ag₂O₄C₂ rings formed by a pair of acetate ligands bridging a pair of silver centres.{{Cite journal |doi = 10.1021/cm052657v|title = The Simple Yet Elusive Crystal Structure of Silver Acetate and the Role of the Ag−Ag Bond in the Formation of Silver Nanoparticles during the Thermally Induced Reduction of Silver Carboxylates|journal = Chemistry of Materials|volume = 18|issue = 6|pages = 1667–1674|year = 2006|last1 = Olson|first1 = Leif P.|last2 = Whitcomb|first2 = David R.|last3 = Rajeswaran|first3 = Manju|last4 = Blanton|first4 = Thomas N.|last5 = Stwertka|first5 = Barbara J.}}

Reactions

Silver acetate finds use in certain transformations in organic synthesis.{{cite journal|title=Silver(I) Acetate|author1=Mary K. Balmer|author2= Brian A. Roden|author3=Dave G. Seapy|journal=Encyclopedia of Reagents for Organic Synthesis|year=2008|doi=10.1002/047084289X.rs013m.pub2|isbn=978-0471936237}}

=Sulfenamide synthesis=

Silver acetate is used to prepare sulfenamides from disulfides and secondary amines:

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

=Hydrogenation=

A solution of silver acetate in pyridine absorbs hydrogen, producing metallic silver:{{cite journal|last=Wright|first=Leon |author2=Well, Sol |author3=Mills, G.A.|title=Homogeneous Catalytic Hydrogenation III. Activation of Hydrogen by Cuprous and Silver Acetates in Pyridine and Dodecylamine|journal=Journal of Physical Chemistry|year=1955|volume=59|issue=10 |pages=1060–1064|doi=10.1021/j150532a016}}

: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.{{cite journal |doi=10.1021/ol061919b|pmid=17078680|title=Direct Palladium-Catalyzed Ortho-Arylation of Benzylamines|journal=Organic Letters|volume=8|issue=23|pages=5211–5213|year=2006|last1=Lazareva|first1=Anna|last2=Daugulis|first2=Olafs}} This reaction is shorter than previous ortho-arylation methods.

=Oxidative dehalogenation=

Silver acetate can be used to convert certain organohalogen compounds into alcohols. 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 forms the basis of the Woodward cis-hydroxylation. This reaction selectively converts an alkene into a cis-diol.{{cite journal|last1=Woodward|first1=R. B.|last2=Brutcher|first2=F. V.|title=cis-Hydroxylation of a Synthetic Steroid Intermediate with Iodine, Silver Acetate and Wet Acetic Acid|journal=Journal of the American Chemical Society|date=January 1958|volume=80|issue=1|pages=209–211|doi=10.1021/ja01534a053}}

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).{{Cite web|url=https://www.sigmaaldrich.com/technical-documents/articles/materials-science/high-performance-printed-electronics.html|title=Reactive Silver Inks for High-Performance Printed Electronics|website=Sigma-Aldrich|language=en|access-date=2019-08-11}}

Safety

The LD₅₀ of silver acetate in mice is 36.7 mg/kg. Low doses of silver acetate in mice produced hyper-excitability, ataxia, central nervous system depression, labored breathing, and even death.{{cite journal|last=Horner|first=Heidi C.|author2=Roebuck, B.D. |author3=Smith, Roger P. |author4= English, Jackson P. |title=Acute toxicity of some silver salts of sulfonamides in mice and the efficacy of penicillamine in silver poisoning|journal=Drug and Chemical Toxicology|year=1977|volume=6|issue=3|pages=267–277|url=https://scifinder.cas.org/scifinder/view/scifinder/scifinderExplore.jsf|doi=10.3109/01480548309017817|pmid=6628259|url-access=subscription}} 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.{{cite journal|last=Hymowitz|first=Norman|author2=Eckholdt, Haftan |title=Effects of a 2.5-mg Silver Acetate Lozenge on Initial and Long-Term Smoking Cessation|journal=Journal of Preventive Medicine|year=1996|volume=25|pages=537–546|pmid=8888321|doi=10.1006/pmed.1996.0087|issue=5}}{{cite journal |author1=E. J. Jensen |author2=E. Schmidt |author3=B. Pedersen |author4=R. Dahl |year= 1991 |title= Effect on smoking cessation of silver acetate, nicotine and ordinary chewing gum, Influence of smoking history |journal= Psychopharmacology |volume= 104 |pages= 470–474 |doi= 10.1007/BF02245651 |pmid= 1780416 |issue= 4|s2cid=1411297}}