Methylidynephosphane

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,{{cite journal | author = Gier TE | title = HCP, A Unique Phosphorus Compound | journal = J. Am. Chem. Soc. | year = 1961 | doi = 10.1021/ja01468a058 | volume = 83 | pages = 1769–1770 | issue = 7}} 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.{{cite journal | author = Regitz M | title = Phosphaalkynes: new building blocks in synthetic chemistry | journal = Chem. Rev. | doi = 10.1021/cr00099a007 | year = 1990 | volume = 90 | pages = 191–213}} The {{chem2|[OCP]−}} (cyaphate) and {{chem2|[SCP]−}} (thiocyaphate) anions are also known.{{cite journal | author = Hubler K, Schwerdtfeger P. | title = Theoretical Studies of NMR Chemical Shifts and Vibrational Frequencies in λ³-Phosphaalkynes P≡C-R | journal = Inorg. Chem. | year = 1999 | volume = 38 | pages = 157–164 | doi = 10.1021/ic9811291}}

HCP has been detected in the interstellar medium.{{cite journal |doi=10.1086/519561 |title=Discovery of Phosphaethyne (HCP) in Space: Phosphorus Chemistry in Circumstellar Envelopes |date=2007 |last1=Agúndez |first1=Marcelino |last2=Cernicharo |first2=José |last3=Guélin |first3=Michel |journal=The Astrophysical Journal |volume=662 |issue=2 |pages=L91–L94 |bibcode=2007ApJ...662L..91A |hdl=10261/191973 |hdl-access=free}}

While the existence of the molecule had been discussed,H. Albers (1950) Angew. Chemie 62:443-467 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.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 [http://www.mycrandall.ca/faculty/MSchriver/coursewebs/ChemRev99LonePairPi.pdf] {{Webarchive|url=https://web.archive.org/web/20161020002010/http://www.mycrandall.ca/faculty/MSchriver/coursewebs/ChemRev99LonePairPi.pdf |date=2016-10-20}}, accessed 2 July 2014. 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,{{cite book|last1=Ledkovskaia-Astman|first1=Marina|last2=Rosenthal|first2=Charlotte|last3=Zirin|first3=Mary Fleming|title=Dictionary of Russian Women Writers|year=1994|publisher=Greenwood Publishing Group|location=Westport, CT|isbn=978-0-313-26265-4}} and perhaps the first woman to die from her own research.{{cite book|last1=Rayner-Canham|first1=Marelene |last2=Rayner-Canham|first2=Geoffrey|title=Women in Chemistry: Their Changing Roles from Alchemical Times to the Mid-twentieth Century|year=2001|url = https://books.google.com/books?isbn=0941901270|page =64|publisher=Chemical Heritage Foundation|location=Philadelphia|isbn=978-0-941901-27-7}}{{cite book|last1=Ogilvie|first1=Marilyn|last2=Harvey|first2=Joy|author-link=Marilyn Bailey Ogilvie|author2-link=Joy Harvey|title=Biographical Dictionary of Women in Science|date=16 December 2003|isbn=1135963436|page=311|publisher=Routledge |url=https://books.google.com/books?id=rUCUAgAAQBAJ&pg=311}}

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{{Molecules detected in outer space}}

Category:Organophosphanes