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Decamethylferrocene

Decamethylferrocene or bis(pentamethylcyclopentadienyl)iron(II) is a chemical compound with formula or . It is a sandwich compound, whose molecule has an iron(II) cation attached by coordination bonds between two pentamethylcyclopentadienyl anions (, ). It can also be viewed as a derivative of ferrocene, with a methyl group replacing each hydrogen atom of its cyclopentadienyl rings. The name and formula are often abbreviated to DmFc, or .

This compound is a yellow crystalline solid that is used in chemical laboratories as a weak reductant. The iron(II) core is easily oxidized to iron(III), yielding the monovalent cation decamethylferrocenium, and even to higher oxidation states.

Preparation

Decamethylferrocene is prepared in the same manner as ferrocene from pentamethylcyclopentadiene. This method can be used to produce other decamethylcyclopentadienyl sandwich compounds. :2 Li(C5Me5) + FeCl2 → Fe(C5Me5)2 + 2 LiCl

The product can be purified by sublimation. has staggered rings. The average distance between iron and each carbon is approximately 2.050 Å. This structure has been confirmed by X-ray crystallography.

Redox reactions

Like ferrocene, decamethylferrocene forms a stable cation because Fe(II) is easily oxidized to Fe(III). Because of the electron donating methyl groups on the groups, decamethylferrocene is more reducing than is ferrocene. In a solution of acetonitrile the reduction potential for the couple is −0.59 V compared to a reference (−0.48 V vs Fc/ in ). Oxygen is reduced to hydrogen peroxide by decamethylferrocene in acidic solution.

Using powerful oxidants (e.g. or in , or in ) decamethylferrocene is oxidized to a stable dication with an iron(IV) core. In the salt, the rings are parallel. In contrast, a tilt angle of 17° between the rings is observed in the crystal structure of the salt.

References

(2014). "Characterization of decamethylferrocene and ferrocene in ionic liquids: argon and vacuum effect on their electrochemical properties". Electrochimica Acta.
(1 August 1999). "The Decamethylferrocenium/Decamethylferrocene Redox Couple: A Superior Redox Standard to the Ferrocenium/Ferrocene Redox Couple for Studying Solvent Effects on the Thermodynamics of Electron Transfer". The Journal of Physical Chemistry B.
(2016). "Isolation and structural and electronic characterization of salts of the decamethylferrocene dication". Science.
(1967). "Organometallic Chemistry of the Transition Metals XXI. Some π-pentamethylcyclopentadienyl Derivatives of Various Transition Metals". [[J. Organomet. Chem.]].
(1979). "Crystal and molecular structures of decamethylmanganocene and decamethylferrocene. Static Jahn-Teller distortion in a metallocene". [[J. Am. Chem. Soc.]].
(1996). "Chemical Redox Agents for Organometallic Chemistry". [[Chem. Rev.]].
(2010). "Oxygen and proton reduction by decamethylferrocene in non-aqueous acidic media". [[Chem. Commun.]].

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ferrocenes pentamethylcyclopentadienyl-complexes one-electron-reducing-agents metallocenes

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