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Ferrocene is the first organometallic compound of the general class metallocene. It was discovered in the middle of the 20th century and is now an enduring favorite among organic chemists.
It is an orange, air stable solid that sublimes on heating and is soluble in normal organic solvents. In the presence of phosphoric acid, it is also a good catalyst in the Friedel-Crafts reaction.
A symmetric and uncharged species, ferrocene has a molecular formula of Fe(e5-C5H5)2 with a single iron 2+ ion sandwiched between two cyclopentadienyl rings in a staggered conformation as shown in Figure 6. This configuration is similar to the staggered configuration in decamethylmetallocenes such as ruthenocene (light yellow, mp 199degC) and osmocene (white, mp 229degC).
In the vapour state, the iron atom is eclipsed by the cyclopentadienyl ring, but x-ray diffraction studies show that it is still held in this staggered structure when crystalline.
Unlike ruthenocene and osmocene, however, the iron atom is not squeezed between the cyclopentadienyl groups but is instead “sandwiched” by the two cyclopentadienyl bonds.
This unusual symmetry, despite the fact that both the iron and the cyclopentadienyl molecules are neutral, makes ferrocene very tolerant to oxidation. The oxidation is reversible, however, and this redox property is the major reason that ferrocene is so widely used in a number of applications, including optical devices, batteries, sensing, catalysis, and medicine.
A number of diacetylated ferrocene derivatives have been synthesized and characterized using NMR and IR spectroscopy. Those with the closest carbonyl positions (i.e., 1,1′-diacetylated ferrocene) are the first to elute from a chromatography column, followed by those with the farthest carbonyl positions.