Phosphinous acid

Last updated
Phosphinous acid
H2POH.png
Names
Other names
hydroxyphosphine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/H3OP/c1-2/h1H,2H2
    Key: RYIOLWQRQXDECZ-UHFFFAOYSA-N
  • OP
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).

Phosphinous acid 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. [1] H2POH is mainly of pedagogical interest. Organophosphinous acids are more prevalent than the parent H2POH.

Organophosphinous acids

Phosphinous acids exist mainly as minor tautomers of secondary phosphine oxides. For example diphenylphosphinous acid, which is not detectable directly, is invoked as the tautomer of diphenylphosphine oxide.

Highly electron-withdrawing substituents stabilize the phosphinous acid tautomer as illustrated by (CF3)2POH. [2]

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<span class="mw-page-title-main">Tautomer</span> Isomers of chemical compounds that interconvert

Tautomers are structural isomers of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life.

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

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

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

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<span class="mw-page-title-main">Phosphorous acid</span> Chemical compound (H3PO3)

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Hypophosphorous acid (HPA), or phosphinic acid, is a phosphorus oxyacid and a powerful reducing agent with molecular formula H3PO2. It is a colorless low-melting compound, which is soluble in water, dioxane and alcohols. The formula for this acid is generally written H3PO2, but a more descriptive presentation is HOP(O)H2, which highlights its monoprotic character. Salts derived from this acid are called hypophosphites.

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

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3
C)
2
C(OH)
2
, a geminal diol.

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

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Martin Arthur Bennett FRS is an Australian inorganic chemist. He gained recognition for studies on the co-ordination chemistry of tertiary phosphines, olefins, and acetylenes, and the relationship of their behaviour to homogeneous catalysis.

<span class="mw-page-title-main">Oxotrichlorobis(triphenylphosphine)rhenium(V)</span> Chemical compound

Oxotrichlorobis(triphenylphosphine)rhenium(V) is the chemical compound with the formula ReOCl3(PPh3)2. This yellow, air-stable solid is a precursor to a variety of other rhenium complexes. In this diamagnetic compound, Re has an octahedral coordination environment with one oxo, three chloro and two mutually trans triphenylphosphine ligands. The oxidation state of rhenium is +5 and its configuration is d2.

<span class="mw-page-title-main">Bis(cyclooctadiene)nickel(0)</span> Chemical compound

Bis(cyclooctadiene)nickel(0) is the organonickel compound with the formula Ni(C8H12)2, also written Ni(cod)2. It is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.

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

Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents.

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

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

Phosphinous acids are usually organophosphorus compounds with the formula R2POH. They are pyramidal in structure. Phosphorus is in the oxidation state III. Most phosphinous acids rapidly convert to the corresponding phosphine oxide, which are tetrahedral and are assigned oxidation state V.

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

Polyfluoroalkoxyaluminates (PFAA) are weakly coordinating anions many of which are of the form [Al(ORF)4]. Most PFAA's possesses an Al(III) center coordinated by four ORF (RF = -CPh(CF3)2 (hfpp), -CH(CF3)2 (hfip), -C(CH3)(CF3)2 (hftb), -C(CF3)3 (pftb)) ligands, giving the anion an overall -1 charge. The most weakly coordinating PFAA is an aluminate dimer, [F{Al(Opftb)3}2], which possess a bridging fluoride between two Al(III) centers. The first PFAA, [Al(Ohfpp)4], was synthesized in 1996 by Steven Strauss, and several other analogs have since been synthesized, including [Al(Ohfip)4], [Al(Ohftb)4], and [Al(Opftb)4] by Ingo Krossing in 2001. These chemically inert and very weakly coordinating ions have been used to stabilize unusual cations, isolate reactive species, and synthesize strong Brønsted acids.

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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.

References

  1. Withnall, Robert; Andrews, Lester (1987). "FTIR spectra of the photolysis products of the phosphine-ozone complex in solid argon". Journal of Physical Chemistry. 91 (4): 784–97. doi:10.1021/j100288a008.
  2. Bader, Julia; Berger, Raphael J. F.; Stammler, Hans-Georg; Mitzel, Norbert W.; Hoge, Berthold (2011). "First Solid-State Structures of Real Diorganyl Phosphinous Acids R2POH (R=CF3, C2F5)". Chemistry - A European Journal. 17 (48): 13420–13423. doi:10.1002/chem.201102370. PMID   22052837.