Cyclopentadienyliron dicarbonyl dimer is an organometallic compound with the formula [(η5-C5H5)Fe(CO)2]2, often abbreviated to Cp2Fe2(CO)4, [CpFe(CO)2]2 or even Fp2, with the colloquial name "fip dimer". It is a dark reddish-purple crystalline solid, which is readily soluble in moderately polar organic solvents such as chloroform and pyridine, but less soluble in carbon tetrachloride and carbon disulfide. Cp2Fe2(CO)4 is insoluble in but stable toward water. Cp2Fe2(CO)4 is reasonably stable to storage under air and serves as a convenient starting material for accessing other Fp (CpFe(CO)2) derivatives (described below).
In solution, Cp2Fe2(CO)4 can be considered a dimeric half-sandwich complex. It exists in three isomeric forms: cis, trans, and an unbridged, open form. These isomeric forms are distinguished by the position of the ligands. The cis and trans isomers differ in the relative position of C5H5 (Cp) ligands. The cis and trans isomers have the formulation [(η5-C5H5)Fe(CO)(μ-CO)]2, that is, two CO ligands are terminal whereas the other two CO ligands bridge between the iron atoms. The cis and trans isomers interconvert via the open isomer, which has no bridging ligands between iron atoms. Instead, it is formulated as (η5-C5H5)(OC)2Fe−Fe(CO)2(η5-C5H5) — the metals are held together by an iron–iron bond. At equilibrium, the cis and trans isomers are predominant.
In addition, the terminal and bridging carbonyls are known to undergo exchange: the trans isomer can undergo bridging–terminal CO ligand exchange through the open isomer, or through a twisting motion without going through the open form. In contrast, the bridging and terminal CO ligands of the cis isomer can only exchange via the open isomer.
In solution, the cis, trans, and open isomers interconvert rapidly at room temperature, making the molecular structure fluxional. The fluxional process for cyclopentadienyliron dicarbonyl dimer is faster than the NMR time scale, so that only an averaged, single Cp signal is observed in the 1H NMR spectrum at 25 °C.
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A cyclopentadienyl complex is a coordination complex of a metal and cyclopentadienyl groups (C5H5−, abbreviated as Cp−). Cyclopentadienyl ligands almost invariably bind to metals as a pentahapto (η5-) bonding mode. The metal–cyclopentadienyl interaction is typically drawn as a single line from the metal center to the center of the Cp ring. Biscyclopentadienyl complexes are called metallocenes. A famous example of this type of complex is ferrocene (FeCp2), which has many analogues for other metals, such as chromocene (CrCp2), cobaltocene (CoCp2), and nickelocene (NiCp2).
Ferrocene is an organometallic compound with the formula . The molecule is a complex consisting of two cyclopentadienyl rings bound to a central iron atom. It is an orange solid with a camphor-like odor, that sublimes above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cation .
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well.
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