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Ferrocene is an orange coloured diamagnetic solid which sublimes at temperatures greater than 100 degC. It is a metallocene with the molecular formula Fe(e5-C5H5)2.
In ferrocene, iron is sandwiched between two cyclopentadienyl (Cp) rings in staggered conformation. Both cp rings are symmetrically bonded to the iron through all of the five carbon atoms, and each ring has a delocalised p-system built from the pz orbitals on the carbon atoms.
X-ray diffraction studies indicate that ferrocene has a D5d configuration, with alternating dihedral angles of +30deg and -80deg for the cyclopentadienyl rings, which are arranged in a pyramidal manner. The benzene core has a chair conformation with dihedral angles of 14deg and displays bond length alternation between 142.7 pm and 141.1 pm, both indicative of steric crowding around the substituents.
Mossbauer spectroscopy indicates that the oxidation state of the iron center in ferrocene is +2 (see p. 937).
Each cyclopentadienyl ring in ferrocene has six p-electrons. This is in accordance with Huckel’s rule for aromaticity, and ferrocene has an 18-electron configuration.
Ferrocene is a stable compound which undergoes many reactions characteristic of aromatic compounds. These include Friedel-Crafts reactions with acetic anhydride, phosphoric acid as the catalyst, and Mannich reactions. In addition, ferrocene is useful as an intermediate in the synthesis of a variety of high temperature polymers, and as an antiknock additive for gasoline. It is also an effective smoke-reduction agent in diesel fuel, promoting the smoke-free combustion of diesel and reducing the amount of smoke produced by tobacco in boilers and engines.