Copper(II) acetate

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Copper(II) acetate
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Small crystals of anhydrous copper(II) acetate
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Copper(II) acetate monohydrate, crystalline
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Copper(II) acetate monohydrate, milled
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Closeup crystals of copper(II) acetate monohydrate
Names
IUPAC name
Tetra-μ2-acetatodiaquadicopper(II)
Other names
Copper(II) ethanoate
Cupric acetate
Copper acetate
Verdigris
Identifiers
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3D model (JSmol)
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EC Number Page Template:Plainlist/styles.css has no content.
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UN number 3077
  • InChI=1S/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 checkY
    Key: OPQARKPSCNTWTJ-UHFFFAOYSA-L checkY
  • InChI=1/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
    Key: OPQARKPSCNTWTJ-NUQVWONBAO
  • [O+]1C(C)O[Cu-3]23([OH2+])[O+]C(C)O[Cu-3]1([OH2+])(OC(C)[O+]2)OC(C)[O+]3
Properties
Cu(CH3COO)2
Molar mass 181.63 g/mol (anhydrous)
199.65 g/mol (hydrate)
Appearance Dark green crystalline solid
Odor Odorless (hydrate)
Density 1.882 g/cm3 (hydrate)
Melting point 115 °C (anhydrous) [1]

Undetermined (hydrate)[2]

Boiling point 240 °C (464 °F; 513 K)
Hydrate:
7.2 g/100Template:NnbspmL (cold water)
20 g/100Template:NnbspmL (hot water)
Solubility Soluble in alcohol
Slightly soluble in ether and glycerol
1.545 (hydrate)
Structure
Monoclinic
Hazards
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2
0
0
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
710 mg/kg oral rat[3]
NIOSH (US health exposure limits):[4]
PEL (Permissible)
 TWA 1 mg/m3 (as Cu)
REL (Recommended)
 TWA 1 mg/m3 (as Cu)
IDLH (Immediate danger)
 TWA 100 mg/m3 (as Cu)
Safety data sheet (SDS) Baker MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Page Module:Chem2/styles.css has no content.Cu(OAc)2 where Page Module:Chem2/styles.css has no content.AcO− is acetate (Page Module:Chem2/styles.css has no content.CH3CO−2). The hydrated derivative, Page Module:Chem2/styles.css has no content.Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially. Anhydrous copper(II) acetate is a dark green crystalline solid, whereas Page Module:Chem2/styles.css has no content.Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as fungicides and green pigments. Today, copper acetates are used as reagents for the synthesis of various inorganic and organic compounds.[5] Copper acetate, like all copper compounds, emits a blue-green glow in a flame.

Occurrence

The mineral hoganite is a naturally occurring form of copper(II) acetate.[6][7] A related mineral, also containing calcium, is paceite.[7] Both are very rare.[8][9]

Structure

File:Copper(II)-acetate-3D-balls2.png
Copper(II) acetate structure

Copper acetate hydrate adopts the paddle wheel structure seen also for related Rh(II) and Cr(II) tetraacetates.[10][11] One oxygen atom on each acetate is bound to one copper atom at 1.97 Å (0.197 nm). Completing the coordination sphere are two water ligands, with Page Module:Chem2/styles.css has no content.Cu-O distances of 2.20 Å (0.220 nm). The two copper atoms are separated by only 2.62 Å (0.262 nm), which is close to the Page Module:Chem2/styles.css has no content.Cu-Cu separation in metallic copper.[12][13][14][15] The two copper centers interact resulting in a diminishing of the magnetic moment such that at temperatures below 90 K (−297.7 °F), Page Module:Chem2/styles.css has no content.Cu2(OAc)4(H2O)2 is essentially diamagnetic. Page Module:Chem2/styles.css has no content.Cu2(OAc)4(H2O)2 was a critical step in the development of modern theories for antiferromagnetic exchange coupling, which ascribe its low-temperature diamagnetic behavior to cancellation of the two opposing spins on the adjacent copper atoms.[16]

Synthesis

Copper(II) acetate is prepared industrially by heating copper(II) hydroxide or basic copper(II) carbonate with acetic acid.[5]

Uses

Organic synthesis

Copper(II) acetate has found some use as an oxidizing agent in organic syntheses. In the Eglinton reaction Page Module:Chem2/styles.css has no content.Cu2(OAc)4 is used to couple terminal alkynes to give a 1,3-diyne:[17][18]

Page Module:Chem2/styles.css has no content.Cu2(OAc)4 + 2 RC≡CH → 2 CuOAc + RC≡C−C≡CR + 2 HOAc

The reaction proceeds via the intermediacy of copper(I) acetylides, which are then oxidized by the copper(II) acetate, releasing the acetylide radical. A related reaction involving copper acetylides is the synthesis of ynamines, terminal alkynes with amine groups using Cu2(OAc)4.[19] It has been used for hydroamination of acrylonitrile.[20]

Chemical analysis

In chemical analysis, it serves as an oxidizing agent in both the Barfoed's test for presence of monosaccharides and as a precursor to a copper-fatty acid complex in the colorimetric copper soap assay to test for free fatty acids.[21]

Other

A mixture of copper acetate and ammonium chloride is used to chemically color copper with a bronze patina.[22]

Copper(I) acetate

Heating a mixture of anhydrous copper(II) acetate and copper metal affords copper(I) acetate:[23][24]

Page Module:Chem2/styles.css has no content.Cu + Cu(OAc)2 → 2 CuOAc

Unlike the copper(II) derivative, copper(I) acetate is colourless and diamagnetic.

Basic copper acetate

"Basic copper acetate" is prepared by neutralizing an aqueous solution of copper(II) acetate. The basic acetate is poorly soluble. This material is a component of verdigris, the blue-green substance that forms on copper during long exposures to atmosphere.[citation needed]

Copper acetoarsenite

Copper(II) acetate reacts with arsenic trioxide to form copper acetoarsenite, a powerful insecticide and fungicide called Paris green.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Copper(II) acetate | C4H6CuO4 | ChemSpider".
  2. ^ Page Module:Citation/CS1/styles.css has no content.Trimble, R. F. (1976). "Copper(II) acetate monohydrate - An erroneous melting point". Journal of Chemical Education. 53 (6): 397. Bibcode:1976JChEd..53..397T. doi:10.1021/ed053p397.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Mineral Safety Data Sheet: Copper (II) Acetate, Monohydrate" (PDF). Archived from the original (PDF) on 2011-09-28. Retrieved 2011-06-14.
  4. ^ Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b Script error: No such module "Template wrapper".
  6. ^ Page Module:Citation/CS1/styles.css has no content.Musumeci, Anthony; Frost, Ray L. (2007-05-01). "A spectroscopic and thermoanalytical study of the mineral hoganite". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 67 (1): 48–57. Bibcode:2007AcSpA..67...48M. doi:10.1016/j.saa.2006.05.037. ISSN 1386-1425. PMID 17321784.
  7. ^ a b Page Module:Citation/CS1/styles.css has no content.Hibbs, D. E.; Kolitsch, U.; Leverett, P.; Sharpe, J. L.; Williams, P. A. (June 2002). "Hoganite and paceite, two new acetate minerals from the Potosi mine, Broken Hill, Australia". Mineralogical Magazine. 66 (3): 459–464. Bibcode:2002MinM...66..459H. doi:10.1180/0026461026630042. ISSN 0026-461X. S2CID 97116531.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Paceite".
  9. ^ Page Module:Citation/CS1/styles.css has no content."List of Minerals". 21 March 2011.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Van Niekerk, J. N.; Schoening, F. R. L. (1953). "X-Ray Evidence for Metal-to-Metal Bonds in Cupric and Chromous Acetate". Nature. 171 (4340): 36–37. Bibcode:1953Natur.171...36V. doi:10.1038/171036a0. S2CID 4292992.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Wells, A. F. (1984). Structural Inorganic Chemistry. Oxford: Clarendon Press. ISBN 978-0-19-855370-0.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Catterick, J.; Thornton, P. (1977). "Structures and physical properties of polynuclear carboxylates". Adv. Inorg. Chem. Radiochem. Advances in Inorganic Chemistry and Radiochemistry. 20: 291–362. doi:10.1016/s0065-2792(08)60041-2. ISBN 9780120236206.
  13. ^ Page Module:Citation/CS1/styles.css has no content.van Niekerk, J. N.; Schoening, F. R. L. (1953-03-10). "A new type of copper complex as found in the crystal structure of cupric acetate, Cu2(CH3COO)4.2H2O". Acta Crystallographica. 6 (3): 227–232. Bibcode:1953AcCry...6..227V. doi:10.1107/S0365110X53000715. ISSN 0365-110X.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Meester, Patrice de; Fletcher, Steven R.; Skapski, Andrzej C. (1973-01-01). "Refined crystal structure of tetra-µ-acetato-bisaquodicopper(II)". Journal of the Chemical Society, Dalton Transactions (23): 2575–2578. doi:10.1039/DT9730002575. ISSN 1364-5447.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Brown, G. M.; Chidambaram, R. (1973-11-15). "Dinuclear copper(II) acetate monohydrate: a redetermination of the structure by neutron-diffraction analysis". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 29 (11): 2393–2403. Bibcode:1973AcCrB..29.2393B. doi:10.1107/S0567740873006758. ISSN 0567-7408.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Carlin, R. L. (1986). Magnetochemistry. Berlin: Springer. pp. 77–82. ISBN 978-3642707353.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Stöckel, K.; Sondheimer, F. "[18]Annulene". Organic Syntheses. 54: 1. doi:10.15227/orgsyn.054.0001; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 6, p. 68.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Campbell, I. D.; Eglinton, G. "Diphenyldiacetylene". Organic Syntheses. 45: 39. doi:10.15227/orgsyn.045.0039; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 5, p. 517.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Vogel, P.; Srogl, J. (2005). "Copper(II) Acetate". EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rc194.pub2. ISBN 978-0-470-84289-8..
  20. ^ Page Module:Citation/CS1/styles.css has no content.Heininger, S. A. "3-(o-Chloroanilino)propionitrile". Organic Syntheses. 38: 14. doi:10.15227/orgsyn.038.0014; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 4, p. 146.
  21. ^ Page Module:Citation/CS1/styles.css has no content.Mustafa, Ahmad; Karmali, Amin; Abdelmoez, Wael (2016). "A Sensitive Microplate Assay for Lipase Activity Measurement Using Olive Oil Emulsion Substrate: Modification of the Copper Soap Colorimetric Method". Journal of Oleo Science. 65 (9): 775–784. doi:10.5650/jos.ess16066. ISSN 1347-3352. PMID 27581492.
  22. ^ Page Module:Citation/CS1/styles.css has no content.Budija, Goran. "Collection of formulas for the chemical, electrochemical and heat colouring of metals, the cyanide free immersion plating and electroplating" (PDF). Finishing.com. Retrieved December 30, 2023.
  23. ^ Page Module:Citation/CS1/styles.css has no content.Kirchner, S. J.; Fernando, Q.; Darby, Dana; Dilts, J. A. (2007). "Copper(I) Acetate". In Busch, Daryle H. (ed.). Inorganic Syntheses. Vol. 20 (1 ed.). Wiley. pp. 53–55. doi:10.1002/9780470132517.ch16. ISBN 9780470132517.
  24. ^ Page Module:Citation/CS1/styles.css has no content.Parish, E. J.; Kizito, S. A. (2001). "Copper(I) Acetate". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rc193. ISBN 0471936235.

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