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.
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| Preferred IUPAC name
Tetraphenylphosphanimine | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.017.309 |
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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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
edit- ^ 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.