Decamethylferrocene
Encyclopedia
Decamethylferrocene is a sandwich compound
. In terms of structure and bonding it resembles ferrocene
, but with a methyl group
on each of the carbons of the Cp rings. It is a yellow crystalline solid that is a weak reductant.
. This method can be used to produce other decamethylcyclopentadienyl sandwich compounds.
The product can be purified by sublimation
. FeCp2* has staggered Cp* rings. The average distance between iron and each carbon is approximately 2.050 Å. This structure has been confirmed by X-ray crystallography
.
by decamethylferrocene in acidic solution.
Sandwich compound
In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic covalent bonds to two arene ligands. The arenes have the formula CnHn, substituted derivatives and heterocyclic derivatives...
. In terms of structure and bonding it resembles ferrocene
Ferrocene
Ferrocene is an organometallic compound with the formula Fe2. It is the prototypical metallocene, a type of organometallic chemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds...
, but with a methyl group
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
on each of the carbons of the Cp rings. It is a yellow crystalline solid that is a weak reductant.
Preparation
Decamethylferrocene is prepared in the same manner as ferrocene from pentamethylcyclopentadienePentamethylcyclopentadiene
1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic diolefin with the formula C5Me5H . 1,2,3,4,5-Pentamethylcyclopentadiene is the precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl, which is often denoted as Cp*...
. 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
Sublimation
Sublimation may refer to:* Sublimation , the change from solid to gas without entering liquid phase* Sublimation , the transformation of emotions* Sublimation , a music album by Canvas Solaris-See also:...
. FeCp2* has staggered Cp* rings. The average distance between iron and each carbon is approximately 2.050 Å. This structure has been confirmed by X-ray crystallography
X-ray crystallography
X-ray crystallography is a method of determining the arrangement of atoms within a crystal, in which a beam of X-rays strikes a crystal and causes the beam of light to spread into many specific directions. From the angles and intensities of these diffracted beams, a crystallographer can produce a...
.
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 Cp* groups, decamethylferrocene is more reducing than is ferrocene. In a solution of CH2Cl2, the reduction potential for the [FeCp2*]+/0 couple is -0.59 V compared to a [FeCp2]0/+ reference. Oxygen is reduced to hydrogen peroxideHydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...
by decamethylferrocene in acidic solution.