Tricyclohexylphosphine

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Tricyclohexylphosphine
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Tricyclohexylphosphine-from-xtal-1991-3D-vdW.png
Identifiers
CAS number 2622-14-2 YesY
PubChem 75806
ChemSpider 68315 N
Jmol-3D images Image 1
Image 3
Properties
Molecular formula C18H33P
Molar mass 280.43 g mol−1
Appearance white solid
Melting point 82 °C (180 °F; 355 K)
Solubility in water organic solvents
Hazards
Main hazards toxic
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

  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.