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Methylidynephosphane

Names
Preferred IUPAC name Methylidynephosphane
Other names Phosphaethyne
Identifiers
CAS Number	6829-52-3
3D model (JSmol)	Interactive image
ChemSpider	122445
PubChem CID	138843
CompTox Dashboard (EPA)	DTXSID80218444
InChI InChI=1S/CHP/c1-2/h1HKey: DPYPSJGRRFKXBE-UHFFFAOYSA-N
SMILES C#P
Properties
Chemical formula	CHP
Molar mass	43.993 g·mol
Conjugate base	Cyaphide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 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. Although isolated samples of methylidynephosphane are impractical, other derivatives have been well studied such as tert-butylphosphaacetylene.

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, 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. The PCO and PCS anions are also known.

HCP has been detected in the interstellar medium.

History

While the existence of the molecule had been discussed, 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. 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, and perhaps the first woman to die from her own research.

References

1. ^ Gier TE (1961). "HCP, A Unique Phosphorus Compound". J. Am. Chem. Soc. 83 (7): 1769–1770. doi:10.1021/ja01468a058.
2. Regitz M (1990). "Phosphaalkynes: new building blocks in synthetic chemistry". Chem. Rev. 90: 191–213. doi:10.1021/cr00099a007.
3. Hubler K, Schwerdtfeger P. (1999). "Theoretical Studies of NMR Chemical Shifts and Vibrational Frequencies in λ-Phosphaalkynes P≡C-R". Inorg. Chem. 38: 157–164. doi:10.1021/ic9811291.
4. 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.
5. H. Albers (1950) Angew. Chemie 62:443-467
6. 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 Archived 2016-10-20 at the Wayback Machine, accessed 2 July 2014.
7. 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.
8. 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.
9. Ogilvie, Marilyn; Harvey, Joy (16 December 2003). Biographical Dictionary of Women in Science. Routledge. p. 311. ISBN 1135963436.

v t e Molecules detected in outer space
Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide Triatomic Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene N2H Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid Five atoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nine atoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Ten atoms or more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuterated molecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
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