Triphenylphosphine phenylimide

Triphenylphosphine phenylimide
Names
	Preferred IUPAC name Tetraphenylphosphanimine
	Other names Tetraphenylphosphine imide; N-(Triphenylphosphoranylidene)benzenamine; (Phenylimino)triphenylphosphorane; N-(Triphenylphosphoranylidene)aniline; N-Phenylimino(triphenyl)phosphorane;
Identifiers
CAS Number	2325-27-1;
3D model (JSmol)	Interactive image;
ChemSpider	67888;
ECHA InfoCard	100.017.309
EC Number	219-039-1;
PubChem CID	75352;
UNII	6L9PT46NGV ;
CompTox Dashboard (EPA)	DTXSID80177820 ;
	InChI 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;
	SMILES c1ccc(cc1)N=P(c2ccccc2)(c3ccccc3)c4ccccc4;
Properties
Chemical formula	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

Triphenylphosphine phenylimide is the organophosphorus compound with the formula Ph₃P=NPh (Ph = C₆H₅). The compound is classified as a phosphanimine. This white solid is soluble in organic solvents. The compound is a prototype of a large class of Staudinger reagents, resulting from the Staudinger reaction.

The phosphanimines 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

^ Staudinger, H; Meyer, Jules (1919). "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine". Helvetica Chimica Acta. 2: 635–646. doi:10.1002/hlca.19190020164.
^ 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)" (PDF). Zeitschrift für Naturforschung B. 43 (2): 138–148. doi:10.1515/znb-1988-0202.

[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)" (PDF). Zeitschrift für Naturforschung B. 43 (2): 138–148. doi:10.1515/znb-1988-0202.

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