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TRISPHAT

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TRISPHAT
Names
IUPAC name Tetrabutylammonium tris(3,4,5,6-tetrachlorobenzene-1,2-diolato-κO,O)phosphorus(V)
Other names Tetrabutylammonium tris(tetrachlorocatecholato)phosphorus(1−)
Bu4N PHAT
1-Butanaminium, N,N,N-tributyl-, (OC-6-11-Δ)-trisphosphate(1−) (1:1)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.647 Edit this at Wikidata
EC Number
  • tetrabutylammonium salt:: 636-891-3
PubChem CID
CompTox Dashboard (EPA)
InChI
  • tetrabutylammonium salt:: InChI=1S/C18Cl12O6P.C16H36N/c19-1-2(20)8(26)14-13(7(1)25)31-37(32-14,33-15-9(27)3(21)4(22)10(28)16(15)34-37)35-17-11(29)5(23)6(24)12(30)18(17)36-37;1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h;5-16H2,1-4H3/q-1;+1Key: GCGVBYHPNKLLAV-UHFFFAOYSA-N
SMILES
  • O1c0c(Cl)c(Cl)c(Cl)c(Cl)c0O123(Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O2)Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O3
  • tributylammonium salt:: O1c0c(Cl)c(Cl)c(Cl)c(Cl)c0O123(Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O2)Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O3.CCCC(CCCC)CCCC
  • tetrabutylammonium salt:: CCCC(CCCC)(CCCC)CCCC.C12=C(C(=C(C(=C1Cl)Cl)Cl)Cl)O34(O2)(OC5=C(O3)C(=C(C(=C5Cl)Cl)Cl)Cl)OC6=C(O4)C(=C(C(=C6Cl)Cl)Cl)Cl
Properties
Chemical formula
Molar mass 1011.06
Appearance colourless solid
Solubility in water CH2Cl2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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
4O
2) ligands. This anion can be resolved into the axially chiral 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 H 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 + 5 HCl
H + Bu3N → Bu3NH

Using a chiral amine, the anion can be readily resolved.

References

  1. Ratni, Hassen; Jodry, Jonathan J.; Lacour, Jérôme; Kündig, E. Peter (2000). " Salt, an Efficient NMR Chiral Shift Reagent for Neutral Planar Chiral Tricarbonylchromium Complexes". Organometallics. 19 (19): 3997–3999. doi:10.1021/om000437f.
  2. Favarger, France; Goujon-Ginglinger, Catherine; Monchaud, David; Lacour, Jérôme (2004). "Large-Scale Synthesis and Resolution of TRISPHAT Anion". Journal of Organic Chemistry. 69 (24): 8521–8524. doi:10.1021/jo048641q. PMID 15549835..
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