Tricyclohexylphosphine is the tertiary phosphine with the formula P(C6H11)3. Commonly used as a ligand
In coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...

 in organometallic chemistry
Organometallic chemistry
Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character...

, it is often abbreviated to PCy3, where Cy stands for cyclohexyl
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...

. It is characterized by both high basicity (pKa = 9.7) and a large ligand cone angle
Ligand cone angle
The ligand cone angle is a measure of the size of a ligand. It is defined as the solid angle formed with the metal at the vertex and the hydrogen atoms at the perimeter of the cone . Tertiary phosphine ligands are commonly classified using this parameter, but the method can be applied to any...


Important compounds containing P(Cy)3 ligands include the 2005 Nobel Prize
Nobel Prize in Chemistry
The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

-winning Grubbs' catalyst
Grubbs' catalyst
Grubbs' Catalyst is a transition metal carbene complex named after Robert H. Grubbs, the chemist who first synthesized it. There are two generations of the catalyst, as shown on the right. In contrast to other olefin metathesis catalysts, Grubbs' Catalysts tolerate other functional groups in the...

 and the homogeneous
Homogeneous catalysis
In chemistry, homogeneous catalysis is a sequence of reactions that involve a catalyst in the same phase as the reactants. Most commonly, a homogeneous catalyst is codissolved in a solvent with the reactants.-Acid catalysis:...

Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...

 catalyst Crabtree's catalyst
Crabtree's catalyst
Crabtree's catalyst is the name given to a complex of iridium with 1,5-cyclooctadiene, tris-cyclohexylphosphine, and pyridine. It is a homogeneous catalyst for hydrogenation reactions, developed by Robert H. Crabtree, a professor at Yale University...

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