TRISPHAT (full name tris(tetrachlorocatecholato)phosphate(1−)) is an inorganic anion with the formula P(O
2C
6Cl
4)−
3 often prepared as the tributylammonium ((C
4H
9)
3NH+
) or tetrabutylammonium ((C
4H
9)
4N+
salt. The anion features phosphorus(V) bonded to three tetrachlorocatecholate (C
6Cl
4O2−
2) ligands. This anion can be resolved into the axially chiral enantiomers, which are optically stable (the picture shows the Δ enantiomer).
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Names | |||
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IUPAC name
Tetrabutylammonium tris(3,4,5,6-tetrachlorobenzene-1,2-diolato-κ2O1,O2)phosphorus(V)
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Other names
Tetrabutylammonium tris(tetrachlorocatecholato)phosphorus(1−)
Bu4N+ PHAT− 1-Butanaminium, N,N,N-tributyl-, (OC-6-11-Δ)-tris[3,4,5,6-tetrachloro-1,2-benzenediolato(2-)-κO1,κO2]phosphate(1−) (1:1) | |||
Identifiers | |||
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3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.164.647 | ||
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
[C16H36N][C18Cl12O6P] | |||
Molar mass | 1011.06 | ||
Appearance | colourless solid | ||
CH2Cl2 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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The TRISPHAT anion has been used as a chiral shift reagent for cations.[1] It improves the resolution of 1H NMR spectra by forming diastereomeric ion pairs.
The anion is prepared by treatment of phosphorus pentachloride with tetrachlorocatechol followed by a tertiary amine gives the anion:
Using a chiral amine, the anion can be readily resolved.[2]