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Silver acetate

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Dec 16, 2021
article - Silver acetate

Silver acetate is an 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.

Silver acetate
Names
IUPAC name

Silver(I) acetate
Systematic IUPAC name

Silver(I) ethanoate
Other names

Acetic acid, silver(I) salt
Silver ethanoate
Argentous acetate
Argentous ethanoate
Identifiers
  • 563-63-3 Y
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.414
EC Number
  • 209-254-9
RTECS number
  • AJ4100000
UNII
  • InChI=1S/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Y
    Key: CQLFBEKRDQMJLZ-UHFFFAOYSA-M Y
  • InChI=1/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
    Key: CQLFBEKRDQMJLZ-REWHXWOFAJ
  • ionic monomer: CC(=O)[O-].[Ag+]
  • coordination dimer without Ag-Ag bond: Cc0[o+][Ag-]oc(C)[o+][Ag]o0
  • coordination dimer with Ag-Ag bond: Cc0[o+][Ag-]1oc(C)[o+][Ag]1o0
Properties
AgC2H3O2
Molar mass 166.912 g/mol
Appearance white to slightly grayish powder
slightly acidic odor
Density 3.26 g/cm3, solid
Boiling point decomposes at 220 °C
1.02 g/100 mL(20 °C)
1.94×103[1]
60.4·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)

not listed
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
Chemical compound

. . . Silver acetate . . .

Silver acetate can be synthesized by the reaction of acetic acid and silver carbonate.[2]

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.[3]

Silver acetate finds use in certain transformations in organic synthesis.[4]

Silver acetate is used to prepare sulfenamides from disulfides and secondary amines:[4]

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

A solution of silver acetate in pyridine absorbs hydrogen, producing metallic silver:[5]

2 CH3CO2Ag + H2 → 2 Ag + 2 CH3CO2H

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.[6] This reaction is shorter than previous ortho-arylation methods.

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.

Silver acetate in combination with iodine forms the basis of the Woodward cis-hydroxylation. This reaction selectively converts an alkene into a cis-diol.[7]

. . . Silver acetate . . .

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. . . Silver acetate . . .