Phosphonium
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| Names | |
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| Systematic IUPAC name | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| 292 | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| PH+ 4 | |
| Molar mass | 35.00552 g mol-1 |
| Related compounds | |
Other cations
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Ammonium |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The phosphonium (more obscurely: phosphinium) cation describes polyatomic cations with the chemical formula PR+
4.[2] Salts of the parent PH4+ are rarely encountered, but this ion is an intermediate in the preparation of the industrially useful tetrakis(hydroxymethyl)phosphonium chloride:
- PH3 + HCl + 4 CH2O → P(CH2OH)4+Cl-
Organic phosphonium salts are common reagents in the laboratory. Those with a P-H bond are produced through protonation of phosphines:
- PR3 + H+ → HPR3+
Many organic quaternary phosphonium cations (P+
R
4) are produced by alkylation of organophosphines. For example the reaction of triphenylphosphine with methyl iodide gives methyltriphenylphosphonium iodide, the precursor to a Wittig reagent:
- PPh3 + CH3I → CH3PPh3+I-
The cation tetraphenylphosphonium (PPh4+) is a useful precipitating agent, analogous to quaternary ammonium salts used in phase transfer catalysis.
See also
- Ammonium (NH4+)
- Hydronium (H3O+)
- Onium compounds
References
- ^ a b "phosphonium (CHEBI:30282)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- ^ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.
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