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Hexaphenylcarbodiphosphorane

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Organophosphorus compound.
Hexaphenylcarbodiphosphorane
Names
Preferred IUPAC name Methanediylidenebis(triphenyl-λ-phosphane)
Other names bis(triphenylphosphoranylidene)methane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C37H30P2/c1-7-19-32(20-8-1)38(33-21-9-2-10-22-33,34-23-11-3-12-24-34)31-39(35-25-13-4-14-26-35,36-27-15-5-16-28-36)37-29-17-6-18-30-37/h1-30HKey: KGZNGAKXXXNCGK-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)P(=C=P(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6
Properties
Chemical formula C37H30P2
Molar mass 536.595 g·mol
Appearance yellow solid
Density 1.205 g/cm
Melting point 198–201 °C (388–394 °F; 471–474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Hexaphenylcarbodiphosphorane is the organophosphorus compound with the formula C(PPh3)2 (where Ph = C6H5). It is a yellow, moisture-sensitive solid. The compound is classified as an ylide and as such carries significant negative charge on carbon. It is isoelectronic with bis(triphenylphosphine)iminium. The P-C-P angle is 131°. The compound has attracted attention as an unusual ligand in organometallic chemistry.

The pure compound has two crystalline phases: a metastable monoclinic C2 phase that is triboluminescent, and an orthorhombic P222 form that is not. Both polymorphs are photoluminescent, with respective peak wavelengths at 540 and 575 nm.

Preparation

The compound was originally prepared by deprotonation of the phosphonium salt Br using potassium.

An improved procedure entails production of the same double phosphonium salt from methylene bromide. The double deprotonation is effected with potassium amide.

Related compounds

References

  1. Tonner, Ralf; Oexler, Florian; Neumueller, Bernhard; Petz, Wolfgang; Frenking, Gernot (2006). "Carbodiphosphoranes: The Chemistry of Divalent Carbon(0)". Angewandte Chemie International Edition. 45 (47): 8038–8042. doi:10.1002/anie.200602552. PMID 17075933.
  2. Petz, W.; Frenking, G. (2010). "Carbodiphosphoranes and Related Ligands". Transition Metal Complexes of Neutral eta1-Carbon Ligands. Topics in Organometallic Chemistry. Vol. 30. pp. 49–92. Bibcode:2010tmcn.book...49P. doi:10.1007/978-3-642-04722-0_3. ISBN 978-3-642-04721-3. {{cite book}}: |journal= ignored (help)
  3. Hardy, Gordon E.; Kaska, William C.; Chandra, B. P.; Zink, Jeffrey I. (March 1981). "Triboluminescence-structure relationships in polymorphs of hexaphenylcarbodiphosphorane and anthranilic acid, molecular crystals, and salts". Journal of the American Chemical Society. 103 (5): 1074–1079. doi:10.1021/ja00395a014.
  4. Ramirez, Fausto; Desai, N. B.; Hansen, B.; McKelvie, N. (1961). "Hexaphenylcarbodiphosphorane, (C6H5)3P:C:P(C6H5)3". Journal of the American Chemical Society. 83 (16): 3539–40. doi:10.1021/ja01477a052.
  5. Gruber, Marco; Bauer, Walter; Maid, Harald; Schöll, Kilian; Tykwinski, Rik R. (2017). "Synthetic and NMR Studies on Hexaphenylcarbodiphosphorane (Ph3P=C=PPh3)". Inorganica Chimica Acta. 468: 152–158. doi:10.1016/j.ica.2017.04.018.
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