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 Ph
3P=NPh (
Ph = C
6H
5). 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 phosphine imides were first prepared in the laboratory of Nobelist
Hermann Staudinger. 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 ...
with
phenylazide
Phenyl azide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It is a pale yellow oily liquid with a pungent odor. The structure consists of a linear azide substituent bound to a phenyl group. The Câ ...
.
:Ph
3P + N
3Ph → Ph
3P=NPh + N
2
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