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Title: Methylidynephosphane  
Author: World Heritage Encyclopedia
Language: English
Subject: Methyl isocyanide, Octatetraynyl radical, Triatomic molecule, Interstellar formaldehyde, Propionaldehyde
Publisher: World Heritage Encyclopedia


Methylidynephosphane chemical structure Space filling model
CAS number
PubChem  YesY
ChemSpider  YesY
Jmol-3D images Image 1
Molecular formula CHP
Molar mass 43.99 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

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


Methylidynephosphane is the phosphorus analogue of [2] The PCO and PCS anions are also known.[3]


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 the 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]


  1. ^ a b Gier TE (1961). "HCP, A Unique Phosphorus Compound".  
  2. ^ Regitz M (1990). "Phosphaalkynes: new building blocks in synthetic chemistry".  
  3. ^ Hubler K, Schwerdtfeger P. (1999). "Theoretical Studies of NMR Chemical Shifts and Vibrational Frequencies in λ3-Phosphaalkynes P≡C-R".  
  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.
  6. ^ Ledkovskaia-Astman, Marina; Rosenthal, Charlotte; Zirin, Mary Fleming (1994). Dictionary of Russian Women Writers. Westport, CT: Greenwood Publishing Group.  
  7. ^ 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.  
  8. ^ Ogilvie, Marilyn. Biographical Dictionary of Women in Science. p. 311.  
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