Tricyclohexylphosphine

Tricyclohexylphosphine
Names
IUPAC name
Tricyclohexylphosphane
Other names
P(Cy)3
PCy3
Identifiers
2622-14-2 Yes
ChemSpider 68315 
Jmol-3D images Image
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PubChem 75806
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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]

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. ↑ C. A. Streuli, "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry", Analytical Chemistry 1960, volume 32, pages 985-987.doi:10.1021/ac60164a027
  2. ↑ R. C. Bush and R. J. Angelici (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". Inorganica Chimica Acta 25: L41–42. doi:10.1016/S0020-1693(00)95635-4.