Phosphinous acid is the
inorganic compound
In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds, that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as '' inorganic chemist ...
with the formula H
2POH. It exists, fleetingly, as a mixture with its less stable tautomer H
3PO (
phosphine oxide
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).
Structure and bonding ...
). This mixture has been generated by low temperature oxidation of
phosphine
Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...
with
ozone
Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lo ...
. H
2POH is mainly of pedagogical interest. Organophosphinous acids are more prevalent than the parent H
2POH.
Organophosphinous acids
Phosphinous acids 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 tet ...
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
Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents.
Synthesis
Diphenylphosphine oxide can be prepared by the reaction of phosphonic esters, such as d ...
.
Highly electron-withdrawing substituents stabilize the phosphinous acid tautomer as illustrated by (CF
3)
2POH.
[{{cite journal , doi=10.1002/chem.201102370, title=First Solid-State Structures of Real Diorganyl Phosphinous Acids R2POH (R=CF3, C2F5), year=2011, last1=Bader, first1=Julia, last2=Berger, first2=Raphael J. F., last3=Stammler, first3=Hans-Georg, last4=Mitzel, first4=Norbert W., last5=Hoge, first5=Berthold, journal=Chemistry - A European Journal, volume=17, issue=48, pages=13420–13423, pmid=22052837]
References
Functional groups
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