Tricyclohexylphosphine

Tricyclohexylphosphine
Names
Preferred IUPAC name
Tricyclohexylphosphane
Other names
P(Cy)3
PCy3
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.246 Edit this at Wikidata
UNII
  • InChI=1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2 ☒N
    Key: WLPUWLXVBWGYMZ-UHFFFAOYSA-N ☒N
  • InChI=1/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2
    Key: WLPUWLXVBWGYMZ-UHFFFAOYAM
  • C1(CCCCC1)P(C2CCCCC2)C3CCCCC3
  • C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
Properties
C18H33P
Molar mass 280.43 g mol−1
Appearance white solid
Melting point 82 °C (180 °F; 355 K)
organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

  • Grubbs' catalyst (first generation)
    Grubbs' catalyst (first generation)
  • Crabtree's catalyst
    Crabtree's catalyst

References

  1. ^ Streuli, C. A. (1960). "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry". Anal. Chem. 32 (8): 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.