乙酸銀

乙酸銀
別名	醋酸銀
識別
CAS號	563-63-3
PubChem	11246
ChemSpider	10772
SMILES	CC(=O)[O-].[Ag+];
InChI	1/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1;
InChIKey	CQLFBEKRDQMJLZ-REWHXWOFAJ
EINECS	209-254-9
RTECS	AJ4100000
性質
化學式	AgC2H3O2
摩爾質量	166.912 g/mol g·mol⁻¹
外觀	米黃色固體; 有微酸性氣味
密度	3.259 g/cm3
沸點	220 °C（分解）
溶解性（水）	1.02 g/100 mL(20 °C)
危險性
警示術語	R：R37/38, R41, R50
安全術語	S：S26, S39, S61
歐盟分類	Xi N
	GHS危險性符號;
H-術語	H315, H319, H335, H400
P-術語	P261, P273, P305+351+338
NFPA 704	0 1 0
	致死量或濃度：
LD50（中位劑量）	36.7 mg/kg (小鼠)
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

乙酸銀，又名醋酸銀，是無機化合物，結構式為CH₃COOAg（或AgC₂H₃O₂）。它是一種光敏感的白色晶狀固體。它是一種有用的試劑，在實驗室中作為水溶性銀離子源，氧化陰離子。它已被用於一些戒煙藥物中。

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乙酸銀可以由乙酸和碳酸銀在45–60 °C反應合成。冷卻至室溫後，產物以固體析出^[3]。

{\mathsf {Ag_{2}CO_{3}+2CH_{3}COOH\ {\xrightarrow {}}\ 2AgCH_{3}COO+CO_{2}\uparrow +H_{2}O}}

它也可以在濃硝酸銀水溶液中與乙酸鈉作用，生成沉澱製得。

乙酸銀的結構為一對乙酸配體橋接中心的兩個銀，形成八元Ag₂O₄C₂環^[4]。

羰基

乙酸銀與一氧化碳（CO）一起，可以誘導伯和仲胺的羰基化。也可以使用其它銀鹽，但乙酸銀產率最好。

{\mathsf {2R_{2}NH+2AgOAc+CO\ {\xrightarrow {}}\ [R_{2}N]_{2}CO+2HOAc+2Ag}}

加氫

乙酸銀在吡啶溶液中吸收氫，並還原出金屬銀^[5]。

直接鄰位芳基化

對於苄胺和N-甲基苄胺，乙酸銀在直接鄰位芳基化（裝在芳環上的兩個相鄰的取代基）中是一種有用的試劑。該反應需要鈀催化，乙酸銀需稍過量^[6]。該反應比以前的鄰位芳基化方法要短。

在醫療領域，乙酸銀被用於口香糖、噴劑和含片，防止吸煙者吸煙。這些產品中的銀，隨着煙進入吸煙者的口腔中，使吸煙者感受到不愉快的金屬味，從而阻止他們吸煙。對500名成年吸煙者超過3個月的時間測試表明，含2.5毫克乙酸銀的含片有「適當的療效」。然而，一個為期12個月的測試卻失敗了。1974年，乙酸銀在歐洲首次作為非處方戒煙含片（Repaton）推出，三年後推出了口香糖（Tabmint）^[7]。

乙酸銀對小鼠的腹腔注射LD₅₀為36.7 mg/kg。低劑量的乙酸銀使小鼠高度興奮，運動失調，中樞神經系統受抑，呼吸困難，甚至死亡^[8]。美國FDA建議，醋酸銀的短時攝入量應限制在756毫克；攝入過多可能會導致銀中毒^[7]^[9]。

[1]
Record of CAS RN 563-63-3 in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）.
[2]
Datenblatt Silberacetat [Silberacetat安全信息單（MSDS）] (PDF). Herstellers Merck. [15. Januar 2012] （德語）.
[3]
Logvinenko, V.; Polunina, O.; Mikhailov, Yu; Mikhailov, K.; Bokhonov, B. Study of Thermal Decomposition of Silver Acetate. Journal of Thermal Analysis and Calorimetry. 2007, 90 (3): 813–816. doi:10.1007/s10973-006-7883-9.
[4]
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
[5]
Wright, Leon; Well, Sol, Mills, G.A. Homogeneous Catalytic Hydrogenation III. Activation of Hydrogen by Cuprous and Silver Acetates in Pyridine and Dodecylamine. Journal of Physical Chemistry. 1955, 59: 1060–1064. doi:10.1021/j150532a016.
[6]
Lazareva, Anna; Daugulis. Olafs. Direct Palladium-Catalyzed Ortho-Arylation of Benzylamines. 2006, 8: 5211–5213. doi:10.1021/o1061919b.
[7]
Hymowitz, Norman; Eckholdt, Haftan. Effects of a 2.5-mg Silver Acetate Lozenge on Initial and Long-Term Smoking Cessation. Journal of Preventitive Medicine. 1996, 25 (5): 537–546. PMID 8888321. doi:10.1006/pmed.1996.0087.
[8]
Horner, Heidi C.; Roebuck, B.D.; Smith, Roger P.; English, Jackson P. Acute toxicity of some silver salts of sulfonamides in mice and the efficacy of penicillamine in silver poisoning. Drug and Chemical Toxicology. 1977, 6: 267–277 [2013-01-25]. （原始內容存檔於2020-04-19）.
[9]
E. J. Jensen, E. Schmidt, B. Pedersen, R. Dahl. Effect on smoking cessation of silver acetate, nicotine and ordinary chewing gum, Influence of smoking history. Psychopharmacology. 1991, 104 (4): 470–474. PMID 1780416. doi:10.1007/BF02245651.

Редкол.: Никольский Б.П. и др. (編). Справочник химика. 2 3-е изд., испр. Л.: Химия. 1971: 1168.
Рипан Р., Четяну И. Неорганическая химия. Химия металлов. 2. М.: Мир. 1972: 871.

F. H. MacDougall, and S. Peterson. Equilibria in Silver Acetate Solutions. The Journal of Physical Chemistry. 1947, 51 (6): 1346–1361. doi:10.1021/j150456a009.

[GESTIS-1] [1]
Record of CAS RN 563-63-3 in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）.

[Merck-2] [2]
Datenblatt Silberacetat [Silberacetat安全信息單（MSDS）] (PDF). Herstellers Merck. [15. Januar 2012] （德語）.

[ref_new-3] [3]
Logvinenko, V.; Polunina, O.; Mikhailov, Yu; Mikhailov, K.; Bokhonov, B. Study of Thermal Decomposition of Silver Acetate. Journal of Thermal Analysis and Calorimetry. 2007, 90 (3): 813–816. doi:10.1007/s10973-006-7883-9.

[4] [4]
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

[ref_9-5] [5]
Wright, Leon; Well, Sol, Mills, G.A. Homogeneous Catalytic Hydrogenation III. Activation of Hydrogen by Cuprous and Silver Acetates in Pyridine and Dodecylamine. Journal of Physical Chemistry. 1955, 59: 1060–1064. doi:10.1021/j150532a016.

[ref_5-6] [6]
Lazareva, Anna; Daugulis. Olafs. Direct Palladium-Catalyzed Ortho-Arylation of Benzylamines. 2006, 8: 5211–5213. doi:10.1021/o1061919b.

[ref_4-7] [7]
Hymowitz, Norman; Eckholdt, Haftan. Effects of a 2.5-mg Silver Acetate Lozenge on Initial and Long-Term Smoking Cessation. Journal of Preventitive Medicine. 1996, 25 (5): 537–546. PMID 8888321. doi:10.1006/pmed.1996.0087.

[ref_3-8] [8]
Horner, Heidi C.; Roebuck, B.D.; Smith, Roger P.; English, Jackson P. Acute toxicity of some silver salts of sulfonamides in mice and the efficacy of penicillamine in silver poisoning. Drug and Chemical Toxicology. 1977, 6: 267–277 [2013-01-25]. （原始內容存檔於2020-04-19）.

[9] [9]
E. J. Jensen, E. Schmidt, B. Pedersen, R. Dahl. Effect on smoking cessation of silver acetate, nicotine and ordinary chewing gum, Influence of smoking history. Psychopharmacology. 1991, 104 (4): 470–474. PMID 1780416. doi:10.1007/BF02245651.

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羰基

加氫

直接鄰位芳基化

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乙酸銀

羰基

加氫

直接鄰位芳基化

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合成與結構

反應

用途

安全

參考文獻

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