Hexaphenylcarbodiphosphorane is the

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

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 Bis(triphenylphosphine)iminium chloride is the chemical compound with the formula , often abbreviated , where Ph is phenyl , or even abbreviated PNl or NPl or PPNCl or PNPCl, where PPN or PNP stands for . This colorless salt is a source of the c ...

. 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 In crystallography, the orthorhombic crystal system is one of the 7 crystal systems. Orthorhombic lattices result from stretching a cubic lattice along two of its orthogonal pairs by two different factors, resulting in a rectangular prism with a r ...

P222 form that is not. Both polymorphs are

photoluminescent Photoluminescence (abbreviated as PL) is light emission from any form of matter after the absorption of photons (electromagnetic radiation). It is one of many forms of luminescence (light emission) and is initiated by photoexcitation (i.e. pho ...

, with respective peak wavelengths at 540 and 575 nm.

Preparation

The compound was originally prepared by deprotonation of the phosphonium salt C(PPh₃)₂r using potassium. An improved procedure entails production of the same double phosphonium salt from methylene bromide. The double deprotonation is effected with potassium amide.{{cite journal , doi=10.1016/j.ica.2017.04.018, title=Synthetic and NMR Studies on Hexaphenylcarbodiphosphorane (Ph₃P=C=PPh₃), year=2017, last1=Gruber, first1=Marco, last2=Bauer, first2=Walter, last3=Maid, first3=Harald, last4=Schöll, first4=Kilian, last5=Tykwinski, first5=Rik R., journal=Inorganica Chimica Acta, volume=468, pages=152–158

Related compounds

* Methylenetriphenylphosphorane (CH₂=PPh₃), the parent Wittig reagent

References

Organophosphorus compounds Ligands