(Benzene)chromium tricarbonyl is an

organometallic compound 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 ...

with the formula . This yellow crystalline solid compound is soluble in common

nonpolar In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more polar ...

organic solvents. The molecule adopts a geometry known as " piano stool" because of the planar arrangement of the

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...

group and the presence of three CO

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

s as "legs" on the chromium-bond axis.

Preparation

(Benzene)tricarbonylchromium was first reported in 1957 by Fischer and Öfele, who prepared the compound by the

carbonylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...

of bis(benzene)chromium. They obtained mainly chromium carbonyl (Cr(CO)) and traces of Cr(CH)(CO). The synthesis was optimized through the reaction of Cr(CO) and Cr(CH). For commercial purposes, a reaction of Cr(CO) and

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

is used: :Cr(CO) + CH → Cr(CH)(CO) + 3 CO

Applications

Complexes of the type (Arene)Cr(CO)₃ have been well investigated as reagents in organic synthesis.. The aromatic ring of (benzene)tricarbonylchromium is substantially more

electrophilic In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carr ...

than benzene itself, allowing it to undergo

nucleophilic addition In organic chemistry, a nucleophilic addition (AN) reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic addit ...

reactions.Herndon, James W; Laurent, Stéphane E. (2008). "(η-Benzene)tricarbonylchromium," in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 2008. . Article Online Posting Date: March 15, 2009 : It is also more acidic, undergoing lithiation upon treatment with ''n''-butyllithium. The resulting

organolithium compound In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

can then be used as a nucleophile in various reactions, for example, with

trimethylsilyl chloride Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula , often abbreviated or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely u ...

: : (Benzene)tricarbonylchromium is a useful

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

for the

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of 1,3-

diene In organic chemistry, a diene ( ); also diolefin, ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nome ...

s. The product

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

results from 1,4-addition of

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

. The complex does not hydrogenate isolated

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

References

{{DEFAULTSORT:Benzenechromium tricarbonyl Half sandwich compounds Organochromium compounds Carbonyl complexes