ferrocene

Molecular Weight of Ferrocene

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molecular weight of ferrocene

The ferrocene molecule is a sandwich-containing compound with the iron atom “sandwiched” between two cyclopentadienyl rings. This is a very important feature of the ferrocene and is also observed in decamethylmetallocenes such as ruthenocene (light-yellow, mp 199degC) and osmocene (white, mp 229degC).

In crystalline ferrocene, the Cp rings freely rotate around the Fe-C bond axis. The ring rotation occurs because of the strong interaction between the two cyclopentadienyl groups. However, when some substituents were introduced into the Cp rings, there is a noticeable change in the rotation property.

One example is the (o-hydroxyphenyl)ferrocene derivative with a hydroxyl group. When the hydroxyl group is replaced by an Al3+, the 1’/b value decreased significantly. In addition, the Al3+ chelate structure reduces the rotation of the unsubstituted Cp ring.

Other ferrocenes with different hydroxyl groups showed similar relationships to the (o-hydroxyphenyl)ferrocene. The Cp ring of these derivatives freely rotates around the Fe-C bond axis, but when a strong chelating metal cation was added to the ferrocene, the Cp ring of the ferrocene would be prevented from rotating by the chelate structure.

The ferrocene derivatives are widely used in the field of organometallic chemistry as bidentate ligands to bind d-block transition metals such as Ni, Pd, and Pt. In this way, ferrocene has been used to promote electrophilic aromatic substitution and nitrosative reduction reactions. It is 100,000 times more reactive than benzene in these reactions. The ferrocene derivatives are also useful as solvents in a variety of chemical and biological applications.

Diacetylferrocene As a DNA Hybridization Label

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Ferrocene is an important substance, with a long history in the material science and chemical sensing fields, among others. It is a relatively nonpolar compound, and can be used in asymmetric catalysis. It also has a unique electrochemical property, which enables it to be an ideal candidate for a DNA hybridization label. There are numerous applications for this substance, ranging from the obvious (asymmetric catalysis) to the obscure (antitumor agents). Some of its derivatives have shown biological activity, and some have been even synthesized in reasonable yields. These include hexa(ferrocenyl)benzene, and the acetyl variant. Among its uses are as a redox mediator for enzyme sensors, as an antitumor agent, and as a molecule able to decode a sequence of DNA molecules, thus allowing for efficient DNA hybridization.

The most practical ferrocene application is in the area of catalysis. Ferrocene derivatives have been used in the production of topoisomerase IIb inhibitors, as well as in the aforementioned DNA hybridization applications. In addition, it has been demonstrated to be an efficient redox mediator for enzyme sensors. In this regard, it is a good candidate for a nucleic acid biosensor, albeit one with some room for improvement. This may be due to its ionic nature. A suitable framework, which would allow for its construction, would be hexasubstituted benzene.

Several companies have produced ferrocene derivatives in varying degrees of success. Astruc offers compounds such as hexa(ferrocenyl)benzene, while American Elements has produced a plethora of standard and specialty grades.


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