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Other names: cyclo­penta­dienyl anion, Cp-


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The cyclopentadienyl anion is the conjugate base of the simple hydrocarbon cyclopentadiene. Unlike most hydrocarbons, cyclopentadiene is fairly acidic and may be readily deprotonated; this is because the resultant cyclopentadieniede ring has 6 electrons in a conjugated π system and, like benzene, satisfies the Hückel criterion for aromatic ring stabilization. Cyclopentadienyl further sees frequent usage as a ligand in organometallic chemistry, where it is acts as a pentahaptic ligand capable of bonding obliquely through its π electron system to form coordination complexes such as ferrocene.