Triphenylphosphine phenylimide

Triphenylphosphine phenylimide is the organophosphorus compound 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.

Triphenylphosphine phenylimide
Names
Preferred IUPAC name
Tetraphenylphosphanimine
Other names
  • Tetraphenylphosphine imide
  • N-(Triphenylphosphoranylidene)benzenamine
  • (Phenylimino)triphenylphosphorane
  • N-(Triphenylphosphoranylidene)aniline
  • N-Phenylimino(triphenyl)phosphorane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.309
EC Number
  • 219-039-1
UNII
  • InChI=1S/C24H20NP/c1-5-13-21(14-6-1)25-26(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
    Key: PTLOPIHJOPWUNN-UHFFFAOYSA-N
  • c1ccc(cc1)N=P(c2ccccc2)(c3ccccc3)c4ccccc4
Properties
C24H20NP
Molar mass 353.405 g·mol−1
Appearance White solid
Density 1.239 g/cm3
Melting point 131–132 °C (268–270 °F; 404–405 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The phosphine imides were first prepared in the laboratory of Nobelist Hermann Staudinger. His synthesis involved the direct reaction of triphenylphosphine with phenylazide. [1]

Ph3P + N3Ph → Ph3P=NPh + N2

X-ray crystallography establishes that the P-N-C angle is bent (130.4°) and the P-N distance is 160 pm.[2]

References
  1. Staudinger, H; Meyer, Jules (1919). "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine". Helvetica Chimica Acta. 2: 635–646. doi:10.1002/hlca.19190020164.
  2. Eberhard Böhm; Kurt Dehnicke; Johannes Beck; Wolfgang Hiller; Joachim Strähle; Andreas Maurer; Dieter Fenske (1988). "Die Kristallstrukturen von Ph3PNPh, [Ph3PN(H)Ph][AuI2], und von 2,3-Bis(triphenylphosphoranimino)maleinsäure-N-methylimid (The Crystal Structures of Ph3PNPh, [Ph3PN(H)Ph][AuI2] and of 2,3-Bis(triphenylphosphoranimino)maleic Acid-N-methylimide)". Zeitschrift für Naturforschung B. 43 (2): 138–148. doi:10.1515/znb-1988-0202.
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