Cyclopentadienyl anion
Aromatic ionic species From Wikipedia, the free encyclopedia
Aromatic ionic species From Wikipedia, the free encyclopedia
In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of [C
5H
5]−
and abbreviated as Cp−.[1] It is formed by the deprotonation of cyclopentadiene. The cyclopentadienyl anion is a ligand which binds to a metal in organometallic chemistry.[2]
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Names | |||
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IUPAC name
Cyclopentadienide | |||
Identifiers | |||
3D model (JSmol) |
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ChemSpider | |||
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |||
[C 5H 5]− or Cp− | |||
Molar mass | 65.09 g/mol | ||
Conjugate acid | Cyclopentadiene | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The cyclopentadienyl anion is a planar, cyclic, regular-pentagonal ion; it has 6 π-electrons (4n + 2, where n = 1), which fulfills Hückel's rule of aromaticity. Each double bond and lone pair provides 2 π-electrons, which are delocalized into the ring.[3]
Cyclopentadiene has a pKa of about 16. It is acidic relative to many carbon acids. The enhanced acidity is attributed to stabilization of the conjugate base, cyclopentadienyl anion.
Cyclopentadienyl anions form a variety of cyclopentadienyl complexes.[4]
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