chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

, the cyclopentadienyl anion or cyclopentadienide is an

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

species with a formula of and abbreviated as Cp⁻. It is formed from the deprotonation of the molecule cyclopentadiene.

Properties

The cyclopentadienyl anion is a planar, cyclic, regular-

pentagon In geometry, a pentagon (from the Greek πέντε ''pente'' meaning ''five'' and γωνία ''gonia'' meaning ''angle'') is any five-sided polygon or 5-gon. The sum of the internal angles in a simple pentagon is 540°. A pentagon may be simpl ...

al ion; it has 6 π-electrons (4''n'' + 2, where ''n'' = 1), which fulfills

Hückel's rule In organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4''n'' + 2 π electrons, where ''n'' is a non-negative integer. The quantum mechanical basis for its formulation was ...

of aromaticity. The structure shown is a composite of five

resonance contributor In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance structures'' or ...

s in which each carbon atom carries part of the negative charge.

Salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...

of the cyclopentadienyl anion can be stable, e.g.,

sodium cyclopentadienide Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp− is the cyclopentadienide anion. Sodium cyclopentadienide is a colorless solid, although samples often are pi ...

. It can also coordinate as a

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 electr ...

metal A metal (from Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. Metals are typicall ...

atoms Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, an ...

, forming coordination compounds known as

cyclopentadienyl complex A cyclopentadienyl complex is a coordination complex of a metal and cyclopentadienyl groups (, abbreviated as Cp−). Cyclopentadienyl ligands almost invariably bind to metals as a pentahapto (''η''5-) bonding mode. The metal–cyclopentadien ...

es. Biscyclopentadienyl complexes are called

metallocene A metallocene is a compound typically consisting of two cyclopentadienyl anions (, abbreviated Cp) bound to a metallic element, metal center (M) in the oxidation state II, with the resulting general formula Closely related to the metallocenes are ...

s. Cyclopentadienyl, , and cyclopentadiene, , can substitute one or more hydrogens, forming derivatives having covalent bonds. (See Cyclopentadiene#Derivatives)

Abbreviation

The abbreviation Cp for cyclopentadienyl played a role in the naming of element 112,

copernicium Copernicium is a synthetic chemical element with the symbol Cn and atomic number 112. Its known isotopes are extremely radioactive, and have only been created in a laboratory. The most stable known isotope, copernicium-285, has a half-life of ap ...

, for which the originally proposed symbol was Cp. However, as Cp⁻ was already in use as the abbreviation for cyclopentadienyl (and Cp had been used for cassiopeium, a former name of

lutetium Lutetium is a chemical element with the symbol Lu and atomic number 71. It is a silvery white metal, which resists corrosion in dry air, but not in moist air. Lutetium is the last element in the lanthanide series, and it is traditionally counted am ...

), the symbol for copernicium was changed to Cn.

References

{{Chemistry-stub Anions Non-benzenoid aromatic carbocycles Simple aromatic rings

Properties

Abbreviation

See also

References