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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Methylidynephosphane | |||
Other names
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| Identifiers | |||
3D model (JSmol) | |||
| ChemSpider | |||
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| Properties | |||
| HCP | |||
| Molar mass | 43.993 g·mol−1 | ||
| Conjugate base | Cyaphide | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Methylidynephosphane (phosphaethyne) is a chemical compound with thechemical formulaHC≡P. It was the firstphosphaalkyne compound discovered, containing the unusualC≡Pcarbon-phosphorustriple bond. Although isolated samples of methylidynephosphane are impractical, other derivatives have been well studied such astert-butylphosphaacetylene. The conjugate base of methylidynephosphane iscyaphide.
Methylidynephosphane is the phosphorus analogue ofhydrogen cyanide, with thenitrile nitrogen replaced by phosphorus. Methylidynephosphane can be synthesized via the reaction ofphosphine 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 astert-butyl ortrimethylsilyl, substituted for the hydrogen atom, are much more stable, and are useful reagents for the synthesis of variousorganophosphorus compounds.[2] The[OCP]− (cyaphate) and[SCP]− (thiocyaphate)anions are also known.[3]
HCP has been detected in theinterstellar medium.[4]
While the existence of the molecule had been discussed,[5] and early attempts had been made to prepare it, methylidynephosphane was first successfully synthesised in 1961, by T.E. Gier ofE. I. duPont de Nemours, Inc.[1][6] Earlier reports of preparing its sodium salt were reported as unreproducible by Gier. Methylidynephosphane may have contributed to an explosion that killedVera Bogdanovskaia, an early chemist pursuing it, one of the first female chemists in Russia,[7] and perhaps the first woman to die from her own research.[8][9]
