Puneet Varma (Editor)

TRISPHAT

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Formula
  
[C16H36N][C18Cl12O6P]

Molar mass
  
1011.06

Appearance
  
colourless solid

Solubility in water
  
CH2Cl2

TRISPHAT httpsuploadwikimediaorgwikipediacommons88

Tributylammonium TRISPHAT is an organic salt with the formula [(C4H9)3NH]+[P(O2C6Cl4)3−]. The anion features phosphorus(V) bonded to three tetrachlorocatecholate (C6Cl4O22−) ligands. This anion can be resolved into the enantiomers, which are optically stable (the picture shows the Δ enantiomer).

The TRISPHAT anion has been used as a chiral shift reagent for cations. It improves the resolution of 1H NMR spectra by forming diastereomeric ion pairs.

Preparation

The anion is prepared by treatment of phosphorus pentachloride with tetrachlorocatechol followed by a tertiary amine gives the anion:

PCl5 + 3 C6Cl4(OH)2 → H[P(O2C6Cl4)3] + 5 HCl

H[P(O2C6Cl4)3] + Bu3N Bu3NH+ [P(O2C6Cl4)3]− Using a chiral amine, the anion can be readily resolved.

References

TRISPHAT Wikipedia
(Text) CC BY-SA