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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 In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
Cu(OAc)2 where AcO is
acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
(). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially.
Anhydrous A substance is anhydrous if it contains no water. Many processes in chemistry can be impeded by the presence of water; therefore, it is important that water-free reagents and techniques are used. In practice, however, it is very difficult to achi ...
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 Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as
fungicide Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality ...
s 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
reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
s for the synthesis of various inorganic and organic compounds. 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 the ...
.


Structure

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 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 elect ...
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, Cu2(OAc)4(H2O)2 is essentially diamagnetic. Cu2(OAc)4(H2O)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 with
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...
.


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 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. 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 Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed t ...
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