Triphenylphosphine phenylimide 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 Ph₃P=NPh ( Ph = C₆H₅). It is a white solid that is soluble in organic solvents. The compound is a prototype of a large class of Staudinger reagents, resulting from the

Staudinger reaction The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry: :R3P + ...

. The phosphine imides were first prepared in the laboratory of Nobelist

Hermann Staudinger Hermann Staudinger (; 23 March 1881 – 8 September 1965) was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry. He is also ...

. His synthesis involved the direct reaction of

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists a ...

with phenylazide. :Ph₃P + N₃Ph → Ph₃P=NPh + N₂

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...

establishes that the P-N-C angle is bent (130.4°) and the P-N distance is 160 pm.{{cite journal, title=Die Kristallstrukturen von Ph₃PNPh, h₃PN(H)PhAuI₂], und von 2,3-Bis(triphenylphosphoranimino)maleinsäure-N-methylimid (The Crystal Structures of Ph₃PNPh, h₃PN(H)PhAuI₂] and of 2,3-Bis(triphenylphosphoranimino)maleic Acid-N-methylimide) , author1=Eberhard Böhm, author2=Kurt Dehnicke, author3=Johannes Beck, author4=Wolfgang Hiller, author5=Joachim Strähle, author6=Andreas Maurer, author7=Dieter Fenske , journal=Zeitschrift für Naturforschung B, volume=43, pages=138–148, issue=2, doi=10.1515/znb-1988-0202, year=1988, doi-access=free

References

Organophosphorus compounds Phenyl compounds