Methylidynephosphane

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Methylidynephosphane
Methylidynephosphane chemical structure
Space filling model
Names
IUPAC name
Methylidynephosphane
Other names
Phosphaethyne
Identifiers
6829-52-3
ChemSpider 122445
Jmol 3D model Interactive image
PubChem 138843
  • InChI=1S/CHP/c1-2/h1H
    Key: DPYPSJGRRFKXBE-UHFFFAOYSA-N
  • C#P
Properties
CHP
Molar mass 43.99 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methylidynephosphane (phosphaethyne) is a chemical compound which was the first phosphaalkyne compound discovered, containing the unusual C≡P carbon-phosphorus triple bond.

Description

Methylidynephosphane is the phosphorus analogue of hydrogen cyanide, with the nitrile nitrogen replaced by phosphorus. Methylidynephosphane can be synthesised via the reaction of phosphine with carbon,[1] but it is extremely reactive and polymerises readily at temperatures above −120 °C. However, several types of derivatives, with bulky groups, such as tert-butyl or trimethylsilyl, substituted for the hydrogen atom, are much more stable, and are useful reagents for the synthesis of various organophosphorus compounds.[2] The PCO and PCS anions are also known.[3]

History

While the existence of the molecule had been discussed,[4] and early attempts had been made to prepare it (see following), methylidynephosphane was first successfully synthesised in this protio form in 1961, by T.E. Gier of E. I. duPont de Nemours, Inc.;[5][1] earlier reports of preparing its sodium salt were reported as unreproducible by this author. Methylidynephosphane may have been a chemical contributing to an explosion that killed Vera Bogdanovskaia, an early chemist pursuing it (with first interest dating to a studentship with Carl Gräbe), one of the first female chemists in Russia,[6] and perhaps the first to die as a result of her own research.[7][8]

References

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  4. H. Albers (1950) Angew. Chemie 62:443-467
  5. Philip P. Power (1999) π-Bonding and the Lone Pair Effect in Multiple Bonds between Heavier Main Group Elements, Chem. Rev. 99(12):3463-3503, esp. 3491, see [1], accessed 2 July 2014.
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