Acetic acid, silver (1+) salt
3D model (Jmol)
|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)|
EU classification (DSD)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Silver acetate is an inorganic compound with the empirical formula CH3CO2Ag (or AgC2H3O2). It is a photosensitive, white, crystalline solid. It is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion. It has been used in some antismoking drugs.
Synthesis and structure
- 2 CH3CO2H + Ag2CO3 → 2 AgO2CCH3 + H2O + CO2
The structure of silver acetate consists of 8-membered Ag2O4C2 rings formed by a pair of acetate ligands bridging a pair of silver centres.
Solid silver acetate decomposes with heat to make silver particles and various gases, depending on the atmosphere present, and decomposes at slightly lower temperatures with increasing humidity. In air, the reaction mainly goes by the following:
- 4 CH3CO2Ag + 7 O2 → 4 Ag + 8 CO2 + 6 H2O
- 2 R2NH + 2 AgOAc + CO → [R2N]2CO + 2 HOAc + 2 Ag
- 2 CH3CO2Ag + H2 → 2 Ag + 2 CH3CO2H
Silver acetate is a useful reagent for direct ortho-arylation (to install two adjacent substituents on an aromatic ring) for of benzylamines and N-methylbenzylamines. The reaction is palladium-catalized and requires a slight excess of silver acetate. This reaction is shorter than previous ortho-arylation methods.
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 in the smoker's mouth, 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).
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. 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.
- Logvinenko, V.; Polunina, O.; Mikhailov, Yu; Mikhailov, K.; Bokhonov, B. (2007). "Study of Thermal Decomposition of Silver Acetate". Journal of Thermal Analysis and Calorimetry. 90 (3): 813–816. doi:10.1007/s10973-006-7883-9.
- Leif P. Olson, David R. Whitcomb, Manju Rajeswaran, Thomas N. Blanton, Barbara J. Stwertka "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" Chem. Mater., 2006, volume 18, pp 1667–1674. doi:10.1021/cm052657v
- Wright, Leon; Well, Sol; Mills, G.A. (1955). "Homogeneous Catalytic Hydrogenation III. Activation of Hydrogen by Cuprous and Silver Acetates in Pyridine and Dodecylamine". Journal of Physical Chemistry. 59: 1060–1064. doi:10.1021/j150532a016.
- Lazareva, Anna; Daugulis (2006). "Olafs". Direct Palladium-Catalyzed Ortho-Arylation of Benzylamines. 8: 5211–5213. doi:10.1021/o1061919b.
- Woodward, R. B.; Brutcher, F. V. (January 1958). "cis-Hydroxylation of a Synthetic Steroid Intermediate with Iodine, Silver Acetate and Wet Acetic Acid". Journal of the American Chemical Society. 80 (1): 209–211. doi:10.1021/ja01534a053.
- Hymowitz, Norman; Eckholdt, Haftan (1996). "Effects of a 2.5-mg Silver Acetate Lozenge on Initial and Long-Term Smoking Cessation". Journal of Preventive Medicine. 25 (5): 537–546. doi:10.1006/pmed.1996.0087. PMID 8888321.
- Horner, Heidi C.; Roebuck, B.D.; Smith, Roger P.; English, Jackson P. (1977). "Acute toxicity of some silver salts of sulfonamides in mice and the efficacy of penicillamine in silver poisoning". Drug and Chemical Toxicology. 6: 267–277.
- E. J. Jensen; E. Schmidt; B. Pedersen; R. Dahl (1991). "Effect on smoking cessation of silver acetate, nicotine and ordinary chewing gum, Influence of smoking history". Psychopharmacology. 104 (4): 470–474. doi:10.1007/BF02245651. PMID 1780416.
- F. H. MacDougall & S. Peterson (1947). "Equilibria in Silver Acetate Solutions". The Journal of Physical Chemistry. 51 (6): 1346–1361. doi:10.1021/j150456a009.
Salts and the ester of the acetate ion