Tricyclohexylphosphine

Tricyclohexylphosphine is the tertiary phosphine with the formula P(C6H11)3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy3, where Cy stands for cyclohexyl. It is characterized by both high basicity (pKa = 9.7)[1] and a large ligand cone angle (170°).[2][3]

Tricyclohexylphosphine
Names
IUPAC name
Tricyclohexylphosphane
Other names
P(Cy)3
PCy3
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.246
Properties
C18H33P
Molar mass 280.43 g mol−1
Appearance white solid
Melting point 82 °C (180 °F; 355 K)
organic solvents
Hazards
Main hazards toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Important complexes containing P(Cy)3 ligands include the 2005 Nobel Prize-winning Grubbs' catalyst and the homogeneous hydrogenation catalyst Crabtree's catalyst.

References

  1. Streuli, C. A. (1960). "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry". Anal. Chem. 32: 985–987. doi:10.1021/ac60164a027.
  2. Bush, R. C.; Angelici, R. J. (1988). "Phosphine basicities as determined by enthalpies of protonation". Inorg. Chem. 27 (4): 681–686. doi:10.1021/ic00277a022.
  3. Immirzi, A.; Musco, A. (1977). "A Method to Measure the Size of Phosphorus Ligands in Coordination Complexes". Inorg. Chim. Acta. 25: L41–42. doi:10.1016/S0020-1693(00)95635-4.
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