Phosphonic acid: Difference between revisions
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'''Editor-In-Chief:''' Henry A. Hoff | |||
==Overview== | |||
In [[inorganic chemistry]], '''phosphonic acid''' is a [[phosphorus]] [[oxoacid]] with a formula of '''H<sub>3</sub>PO<sub>3</sub>''', more commonly known as [[phosphorous acid]]. It exists in solution as two [[tautomer]]s, the major one being HP(O)</sub>(OH)<sub>2</sub> and the minor one P(OH)<sub>3</sub>. The former is sometimes termed ''phosphonic acid'', with the latter designated as ''phosphorous acid''. Sometimes confusingly, both these names are also used to refer to H<sub>3</sub>PO<sub>3</sub> in general, i.e. both tautomers. | In [[inorganic chemistry]], '''phosphonic acid''' is a [[phosphorus]] [[oxoacid]] with a formula of '''H<sub>3</sub>PO<sub>3</sub>''', more commonly known as [[phosphorous acid]]. It exists in solution as two [[tautomer]]s, the major one being HP(O)</sub>(OH)<sub>2</sub> and the minor one P(OH)<sub>3</sub>. The former is sometimes termed ''phosphonic acid'', with the latter designated as ''phosphorous acid''. Sometimes confusingly, both these names are also used to refer to H<sub>3</sub>PO<sub>3</sub> in general, i.e. both tautomers. | ||
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An '''oligophosphonic acid''' refers to a few molecules of phosphonic acid condensed into a molecule with the loss of water. | An '''oligophosphonic acid''' refers to a few molecules of phosphonic acid condensed into a molecule with the loss of water. | ||
A general formula for such oligophosphonic acids is (HPO)<sub>n</sub>O<sub>n-1</sub>(OH)<sub>2</sub>, where n = 2, 3, 4, etc., oligo-. A '''polyphosphonic acid''' can have dozens of such phosphonic acid units condensed in a row with the loss of H<sub>2</sub>O for each unit added on. | |||
An example that incorporates triphosphonic acid: ethane-1,1,2-triphosphonic acid<ref name=Bogdán>{{ cite journal |author=Bogdán Cs, Péczely G, Hägele G |title=Metal Complexes of Ethane and Propane Frame-Substituted Oligophosphonic and Oligophosphonocarboxylic Acids |journal=Phosphorus, Sulfur, and Silicon and the Related Elements |volume=182 |issue=10 |month=Oct |year=2007 |pages=2337-50 |url=http://www.ingentaconnect.com/content/tandf/gpss/2007/00000182/00000010/art00008?crawler=true }}</ref>. In some phosphonic anhydrides (RPO<sub>2</sub>)<sub>3</sub>, R can be tBu, 2-methylphenyl, 2,4,6-trimethylphenyl.<ref name=Diemert>{{ cite journal |author=Diemert K, Kuchen W, Poll W, Sandt F |title=A Convenient Synthesis of Phosphonic Anhydrides - Trimers [RPO2]3 (R = tert-Butyl, 2-Methylphenyl, 2,4,6-Trimethylphenyl): Their Structures and Reaction Products |journal=Eur J Inorgan Chem. |volume=1998 |issue=3 |pages=361-6 |year=1998 |doi=10.1002/(SICI)1099-0682(199803)1998:3<361::AID-EJIC361>3.0.CO;2-T }}</ref> | |||
<gallery> | |||
Image:Diphosphonic Acid.jpg|Diphosphonic acid | |||
Image:Phosphorous-acid-tautomerism-2D.png|[[Tautomer]]s of '''H<sub>3</sub>PO<sub>3</sub>''':<br>phosphonic acid (left)<br>phosphorous acid (right) | |||
Image:Phosphonic-acid-group-2D.png|The general structure of an organic '''phosphonic acid''' | |||
</gallery> | |||
==References== | ==References== | ||
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==See also== | ==See also== | ||
* [[Phosphoric acid]] | * [[Phosphoric acid]] | ||
* [[Phosphorous acid]] | * [[Phosphorous acid]] | ||
* [[Hypophosphorous acid]] | * [[Hypophosphorous acid]] | ||
* [[Phosphinic acid]] | * [[Phosphinic acid]] | ||
* [[Phosphorus oxoacids]] | |||
==External links== | ==External links== | ||
* {{MeshName|Phosphonic+Acid}} | * {{MeshName|Phosphonic+Acid}} | ||
* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3084169 PubChem] | * [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3084169 PubChem] | ||
{{SIB}} | |||
[[Category:Acids]] | [[Category:Acids]] | ||
[[Category:Phosphorus compounds]] | [[Category:Phosphorus compounds]] | ||
[[Category:Oxygen compounds]] | [[Category:Oxygen compounds]] | ||
[[nl:Fosfonzuur]] | [[nl:Fosfonzuur]] | ||
[[ja:ホスホン酸]] | [[ja:ホスホン酸]] | ||
[[pt:Ácido fosfônico]] | [[pt:Ácido fosfônico]] | ||
{{WH}} | |||
{{WS}} | |||
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Editor-In-Chief: Henry A. Hoff
Overview
In inorganic chemistry, phosphonic acid is a phosphorus oxoacid with a formula of H3PO3, more commonly known as phosphorous acid. It exists in solution as two tautomers, the major one being HP(O)(OH)2 and the minor one P(OH)3. The former is sometimes termed phosphonic acid, with the latter designated as phosphorous acid. Sometimes confusingly, both these names are also used to refer to H3PO3 in general, i.e. both tautomers.
In organic chemistry, a phosphonic acid is a compound with the general formula RP(O)(OH)2.
An example of an organic phosphonic acid is Foscarnet.
An oligophosphonic acid refers to a few molecules of phosphonic acid condensed into a molecule with the loss of water.
A general formula for such oligophosphonic acids is (HPO)nOn-1(OH)2, where n = 2, 3, 4, etc., oligo-. A polyphosphonic acid can have dozens of such phosphonic acid units condensed in a row with the loss of H2O for each unit added on.
An example that incorporates triphosphonic acid: ethane-1,1,2-triphosphonic acid[1]. In some phosphonic anhydrides (RPO2)3, R can be tBu, 2-methylphenyl, 2,4,6-trimethylphenyl.[2]
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Diphosphonic acid
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Tautomers of H3PO3:
phosphonic acid (left)
phosphorous acid (right) -
The general structure of an organic phosphonic acid
References
- ↑ Bogdán Cs, Péczely G, Hägele G (2007). "Metal Complexes of Ethane and Propane Frame-Substituted Oligophosphonic and Oligophosphonocarboxylic Acids". Phosphorus, Sulfur, and Silicon and the Related Elements. 182 (10): 2337–50. Unknown parameter
|month=ignored (help) - ↑ Diemert K, Kuchen W, Poll W, Sandt F (1998). "A Convenient Synthesis of Phosphonic Anhydrides - Trimers [RPO2]3 (R = tert-Butyl, 2-Methylphenyl, 2,4,6-Trimethylphenyl): Their Structures and Reaction Products". Eur J Inorgan Chem. 1998 (3): 361–6. doi:10.1002/(SICI)1099-0682(199803)1998:3<361::AID-EJIC361>3.0.CO;2-T.
See also
External links
- Phosphonic+Acid at the US National Library of Medicine Medical Subject Headings (MeSH)
- PubChem