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Ferrocene is an organometallic compound that exhibits a remarkable “sandwich” structure. It is characterised by the two staggered cyclopentadienyl rings, each with a delocalized p-system built from the pz orbitals on the carbon atoms. This p-system can be shifted by substituents introduced on the cyclopentadienyl ligands, resulting in a significant change in the redox potential.
The symmetry of the molecule is D5d, with the two cyclopentadienyl centers staggered with respect to each other. Both ring systems bond symmetrically to the iron through each of the five carbon atoms. The central iron atom is normally considered to be in the +2 oxidation state, shown by Mossbauer spectroscopy.
Each cyclopentadienyl center then is assigned a single negative charge, resulting in twelve p-electrons on the ring system. These p-electrons, along with the six d-electrons on the iron atom, form an 18-electron, inert gas complex that makes it particularly stable.
Various reactions are exhibited by ferrocene, showing that it is a very versatile compound. These include a wide variety of reactions that are characteristic of aromatic compounds.
One of the most useful reactions is metalation by butyllithium, which produces the +1 ferrocenyl carbocation. This reversible oxidation is the basis for many of the electrochemical anion sensors that have been developed to detect anions in non-aqueous environments.
Other applications of ferrocene and its derivatives are in the production of antiknock fuels for petrol engines, which reduce smoke and prevent knocking. These compounds are also used as curing accelerators in the production of unsaturated polyester resins. They are a safe alternative to tetraethyl lead, which was the previous standard fuel additive in cars.