Methylidynephosphane
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| Preferred IUPAC name
Methylidynephosphane | |||
| Other names
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3D model (JSmol)
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| Properties | |||
| HCP | |||
| Molar mass | 43.993 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Methylidynephosphane (phosphaethyne) is a chemical compound with the chemical formula Page Module:Chem2/styles.css has no content.HC≡P. It was the first phosphaalkyne compound discovered, containing the unusual C≡P carbon-phosphorus triple bond. Although isolated samples of methylidynephosphane are impractical, other derivatives have been well studied such as tert-butylphosphaacetylene. The conjugate base of methylidynephosphane is cyaphide.
Description
Methylidynephosphane is the phosphorus analogue of hydrogen cyanide, with the nitrile nitrogen replaced by phosphorus. Methylidynephosphane can be synthesized 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 Page Module:Chem2/styles.css has no content.[OCP]− (cyaphate) and Page Module:Chem2/styles.css has no content.[SCP]− (thiocyaphate) anions are also known.[3]
HCP has been detected in the interstellar medium.[4]
History
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 of E. 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 killed Vera 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]
References
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- ^ a b Page Module:Citation/CS1/styles.css has no content.Gier TE (1961). "HCP, A Unique Phosphorus Compound". J. Am. Chem. Soc. 83 (7): 1769–1770. Bibcode:1961JAChS..83.1769G. doi:10.1021/ja01468a058.
- ^ Page Module:Citation/CS1/styles.css has no content.Regitz M (1990). "Phosphaalkynes: new building blocks in synthetic chemistry". Chem. Rev. 90: 191–213. doi:10.1021/cr00099a007.
- ^ Page Module:Citation/CS1/styles.css has no content.Hubler K, Schwerdtfeger P. (1999). "Theoretical Studies of NMR Chemical Shifts and Vibrational Frequencies in λ3-Phosphaalkynes P≡C-R". Inorg. Chem. 38: 157–164. doi:10.1021/ic9811291.
- ^ Page Module:Citation/CS1/styles.css has no content.Agúndez, Marcelino; Cernicharo, José; Guélin, Michel (2007). "Discovery of Phosphaethyne (HCP) in Space: Phosphorus Chemistry in Circumstellar Envelopes". The Astrophysical Journal. 662 (2): L91–L94. Bibcode:2007ApJ...662L..91A. doi:10.1086/519561. hdl:10261/191973.
- ^ H. Albers (1950) Angew. Chemie 62:443-467
- ^ 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] Script error: No such module "webarchive"., accessed 2 July 2014.
- ^ Page Module:Citation/CS1/styles.css has no content.Ledkovskaia-Astman, Marina; Rosenthal, Charlotte; Zirin, Mary Fleming (1994). Dictionary of Russian Women Writers. Westport, CT: Greenwood Publishing Group. ISBN 978-0-313-26265-4.
- ^ Page Module:Citation/CS1/styles.css has no content.Rayner-Canham, Marelene; Rayner-Canham, Geoffrey (2001). Women in Chemistry: Their Changing Roles from Alchemical Times to the Mid-twentieth Century. Philadelphia: Chemical Heritage Foundation. p. 64. ISBN 978-0-941901-27-7.
- ^ Page Module:Citation/CS1/styles.css has no content.Ogilvie, Marilyn; Harvey, Joy (16 December 2003). Biographical Dictionary of Women in Science. Routledge. p. 311. ISBN 1135963436.
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