Copper(II) acetate, also referred to as cupric acetate, is the
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the
formula Cu(OAc)
2 where AcO
− is
acetate (). The hydrated derivative, Cu
2(OAc)
4(H
2O)
2, which contains one molecule of water for each copper atom, is available commercially.
Anhydrous copper(II) acetate is a dark green
crystalline
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
solid, whereas Cu
2(OAc)
4(H
2O)
2 is more bluish-green. Since ancient times, copper acetates of some form have been used as
fungicides and green
pigment
A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compou ...
s. Today, copper acetates are used as
reagents for the synthesis of various inorganic and
organic compounds
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
.
Copper acetate, like all copper compounds, emits a blue-green glow in a
flame
A flame (from Latin '' flamma'') is the visible, gaseous part of a fire. It is caused by a highly exothermic chemical reaction taking place in a thin zone. When flames are hot enough to have ionized gaseous components of sufficient density they ...
.
Structure
![Kupfer(II)-acetat-Monohydrat, dichroitisch](https://upload.wikimedia.org/wikipedia/commons/d/d3/Kupfer%28II%29-acetat-Monohydrat%2C_dichroitisch.jpg)
Copper acetate hydrate adopts the
paddle wheel structure seen also for related Rh(II) and Cr(II) tetraacetates. One oxygen atom on each acetate is bound to one copper atom at 1.97
Å (197
pm). Completing the
coordination sphere
In coordination chemistry, the first coordination sphere refers to the array of molecules and ions (the ligands) directly attached to the central metal atom. The second coordination sphere consists of molecules and ions that attached in various ...
are two water
ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
s, with Cu–O distances of 2.20 Å (220 pm). The two copper atoms are separated by only 2.62 Å (262 pm), which is close to the Cu–Cu separation in metallic copper. The two copper centers interact resulting in a diminishing of the magnetic moment such that at temperatures below 90 K, Cu
2(OAc)
4(H
2O)
2 is essentially diamagnetic. Cu
2(OAc)
4(H
2O)
2 was a critical step in the development of modern theories for
antiferromagnetic
In materials that exhibit antiferromagnetism, the magnetic moments of atoms or molecules, usually related to the spins of electrons, align in a regular pattern with neighboring spins (on different sublattices) pointing in opposite directions. ...
exchange coupling, which ascribe its low-temperature diamagnetic behavior to cancellation of the two opposing spins on the adjacent copper atoms.
Synthesis
Copper(II) acetate is prepared industrially by heating
copper(II) hydroxide
Copper(II) hydroxide is the hydroxide of copper with the chemical formula of Cu(OH)2. It is a pale greenish blue or bluish green solid. Some forms of copper(II) hydroxide are sold as "stabilized" copper(II) hydroxide, although they likely consist ...
or
basic copper(II) carbonate
Basic copper carbonate is a chemical compound, more properly called copper(II) carbonate hydroxide. It is an ionic compound (a salt) consisting of the ions copper(II) , carbonate , and hydroxide .
The name most commonly refers to the compound w ...
with
acetic acid.
[
]
Related compounds
Heating a mixture of anhydrous copper(II) acetate and copper metal affords copper(I) acetate
Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish- ...
:
:Cu + Cu(OAc)2 → 2 CuOAc
Unlike the copper(II) derivative, copper(I) acetate is colourless and diamagnetic.
"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
Verdigris is the common name for blue-green, copper-based pigments that form a patina on copper, bronze, and brass. The technical literature is ambiguous as to its chemical composition. Some sources refer to "neutral verdigris" as copper(II) ...
, the blue-green substance that forms on copper during long exposures to atmosphere.
Uses in chemical synthesis
Copper(II) acetate has found some use as an oxidizing agent
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...
in organic syntheses. In the Eglinton reaction
The Glaser coupling is a type of coupling reaction. It is by far the oldest acetylenic coupling and is based on cuprous salts like copper(I) chloride or copper(I) bromide and an additional oxidant like oxygen. The base in its original scope is amm ...
Cu2(OAc)4 is used to couple terminal alkynes
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no ...
to give a 1,3- diyne:
:Cu2(OAc)4 + 2 RC≡CH → 2 CuOAc + RC≡C−C≡CR + 2 HOAc
The reaction proceeds via the intermediacy of copper(I) acetylide
Copper(I) acetylide, or cuprous acetylide, is a chemical compound with the formula Cu2 C2. Although never characterized by X-ray crystallography, the material has been claimed at least since 1856. One form is claimed to be a monohydrate with for ...
s, 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. It has been used for hydroamination
In organic chemistry, hydroamination is the addition of an bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene. In the ideal case, hydroamination is atom economical and green. Amines are common in fine ...
of acrylonitrile
Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecula ...
.
It is also an oxidising agent in Barfoed's test
Barfoed's test is a chemical test used for detecting the presence of monosaccharides. It is based on the reduction of copper(II) acetate to copper(I) oxide (Cu2O), which forms a brick-red precipitate.
::RCHO + 2Cu2+ + 2H2O → RCOOH + Cu2O↓ ...
.
It reacts with arsenic trioxide
Arsenic trioxide, sold under the brand name Trisenox among others, is an inorganic compound and medication. As an industrial chemical, whose major uses include in the manufacture of wood preservatives, pesticides, and glass. As a medication, it ...
to form copper acetoarsenite, a powerful insecticide and fungicide called Paris green.
Mineralogy
The mineral hoganite is a naturally occurring form of copper(II) acetate. A related mineral, also containing calcium, is paceite. Both are very rare.
External links
Copper.org – Other Copper Compounds
5 Feb. 2006
6 Feb. 2006
6 Feb. 2006
Australian - National Pollutant Inventory
8 Aug. 2016
USA NIH National Center for Biotechnology Information
8 Aug. 2016
References
{{Copper compounds
Copper(II) compounds
Acetates
Oxidizing agents
Catalysts