Phosphine oxide

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Phosphine oxide
Phosphine-oxide-from-MW-3D-balls.png
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/H3OP/c1-2/h2H3
    Key: MPQXHAGKBWFSNV-UHFFFAOYSA-N
  • [O-][PH3+]
Properties
H3OP
Molar mass 49.997 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phosphine oxide is the inorganic compound with the formula H3PO. Although stable as a dilute gas, liquid or solid samples are unstable. Unlike many other compounds of the type POxHy, H3PO is rarely discussed and is not even mentioned in major sources on main group chemistry. [1]

Contents

H3PO has been detected by mass spectrometry as a reaction product of oxygen and phosphine, [2] by means of FT-IR in a phosphine-ozone reaction [3]

Generation

Phosphine oxide has been claimed as the product of a reaction of phosphine with vanadium oxytrichloride as well as with chromyl chloride. The product was obtained by matrix isolation. [4] It has also been reported relatively stable in a water-ethanol solution by electrochemical oxidation of white phosphorus, where it slowly disproportionates into phosphine and hypophosphorous acid. [5]

Phosphine oxide is reported as an intermediate in the room-temperature polymerization of phosphine and nitric oxide to solid PxHy. [6]

Further reading

Related Research Articles

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<span class="mw-page-title-main">Dinitrogen pentoxide</span> Chemical compound

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Phosphorous acid is the compound described by the formula H3PO3. This acid is diprotic, not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids.

<span class="mw-page-title-main">Carbodiimide</span> Class of organic compounds with general structure RN=C=NR

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<span class="mw-page-title-main">Robinson–Gabriel synthesis</span> Organic reaction

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<span class="mw-page-title-main">Phosphine oxides</span> Class of chemical compounds

Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3). The parent phosphine oxide (H3PO) remains rare and obscure.

<span class="mw-page-title-main">Carbon trioxide</span> Chemical compound

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<span class="mw-page-title-main">Tributylphosphine</span> Chemical compound

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<span class="mw-page-title-main">Mercury(IV) fluoride</span> Chemical compound

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<span class="mw-page-title-main">Tetrakis(hydroxymethyl)phosphonium chloride</span> Chemical compound

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. The cation P(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts. THPC has applications as a precursor to fire-retardant materials, as well as a microbiocide in commercial and industrial water systems.

<span class="mw-page-title-main">Oxocarbon</span> Chemical compounds made of only carbon and oxygen

In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide. Many other stable or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide and mellitic anhydride.

<span class="mw-page-title-main">Radical (chemistry)</span> Atom, molecule, or ion that has an unpaired valence electron; typically highly reactive

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<span class="mw-page-title-main">Germylene</span> Class of germanium (II) compounds

Germylenes are a class of germanium(II) compounds with the general formula :GeR2. They are heavier carbene analogs. However, unlike carbenes, whose ground state can be either singlet or triplet depending on the substituents, germylenes have exclusively a singlet ground state. Unprotected carbene analogs, including germylenes, has a dimerization nature. Free germylenes can be isolated under the stabilization of steric hindrance or electron donation. The synthesis of first stable free dialkyl germylene was reported by Jutzi, et al in 1991.

<span class="mw-page-title-main">Phosphinous acid</span> Chemical compound

Phosphinous acid (or Phosphinol) is the inorganic compound with the formula H2POH. It exists, fleetingly, as a mixture with its less stable tautomer H3PO (phosphine oxide). This mixture has been generated by low temperature oxidation of phosphine with ozone. H2POH is mainly of pedagogical interest. Organophosphinous acids are more prevalent than the parent H2POH.

Hydrophosphination is the insertion of a carbon-carbon multiple bond into a phosphorus-hydrogen bond forming a new phosphorus-carbon bond. Like other hydrofunctionalizations, the rate and regiochemistry of the insertion reaction is influenced by the catalyst. Catalysts take many forms, but most prevalent are bases and free-radical initiators. Most hydrophosphinations involve reactions of phosphine (PH3).

<span class="mw-page-title-main">Phosphorus monoxide</span> Chemical compound

Phosphorus monoxide is an unstable radical inorganic compound with molecular formula PO.

References

  1. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN   978-0-08-037941-8.
  2. Hamilton, Peter A.; Murrells, Timothy P. (1985). "Kinetics and mechanism of the reactions of PH3 with O(3P) and N(4S) atoms". J. Chem. Soc., Faraday Trans. 2 (81): 1531–1541. doi:10.1039/F29858101531.
  3. Withnall, Robert; Andrews, Lester (1987). "FTIR spectra of the photolysis products of the phosphine-ozone complex in solid argon". J. Phys. Chem. 91 (4): 784–797. doi:10.1021/j100288a008.
  4. Kayser, David A.; Ault, Bruce S. (2003). "Matrix Isolation and Theoretical Study of the Photochemical Reaction of PH3 with OVCl3 and CrCl2O2". J. Phys. Chem. A. 107 (33): 6500–6505. Bibcode:2003JPCA..107.6500K. doi:10.1021/jp022692e.
  5. Yakhvarov, D.; Caporali, M.; Gonsalvi, L.; Latypov, S.; Mirabello, V.; Rizvanov, I.; Sinyashin, O.; Stoppioni, P.; Peruzzini, M. (2011). "Experimental Evidence of Phosphine Oxide Generation in Solution and Trapping by Ruthenium Complexes". Angewandte Chemie International Edition. 50 (23): 5370–5373. doi:10.1002/anie.201100822. PMID   21538749.
  6. Zhao, Yi-Lei; Flora, Jason W.; David Thweatt, William; Garrison, Stephen L.; Gonzalez, Carlos; Houk, K. N.; Marquez, Manuel (2009). "Phosphine Polymerization by Nitric Oxide: Experimental Characterization and Theoretical Predictions of Mechanism". Inorg. Chem. 48 (3): 1223–1231. doi:10.1021/ic801917a. PMID   19102679.