TRISPHAT

TRISPHAT
source ↗	source ↗
Names
	IUPAC name Tetrabutylammonium tris(3,4,5,6-tetrachlorobenzene-1,2-diolato-κ2O1,O2)phosphorus(V)
	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
CAS Number	tetrabutylammonium salt:: 301687-57-0 Y;
3D model (JSmol)	Interactive image; tributylammonium salt:: Interactive image; tetrabutylammonium salt:: Interactive image;
ChemSpider	tetrabutylammonium salt:: 35467078;
EC Number	tetrabutylammonium salt:: 636-891-3;
PubChem CID	tetrabutylammonium salt:: 71310446;
CompTox Dashboard (EPA)	tetrabutylammonium salt:: DTXSID80746191;
	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;+1 Key: GCGVBYHPNKLLAV-UHFFFAOYSA-N;
	SMILES O1c0c(Cl)c(Cl)c(Cl)c(Cl)c0O[P-]123(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)c0O[P-]123(Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O2)Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O3.CCCC[N+H](CCCC)CCCC; tetrabutylammonium salt:: CCCC[N+](CCCC)(CCCC)CCCC.C12=C(C(=C(C(=C1Cl)Cl)Cl)Cl)O[P-]34(O2)(OC5=C(O3)C(=C(C(=C5Cl)Cl)Cl)Cl)OC6=C(O4)C(=C(C(=C6Cl)Cl)Cl)Cl;
Properties
Chemical formula	[C16H36N][C18Cl12O6P]
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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

TRISPHAT (full name tris(tetrachlorocatecholato)phosphate(1−)) is an inorganic anion with the formula P(O₂C₆Cl₄)³⁻, often prepared as the tributylammonium ((C₄H₉)₃NH⁺) or tetrabutylammonium ((C₄H₉)₄N⁺) salt. The anion features phosphorus(V) bonded to three tetrachlorocatecholate (C₆Cl₄O2−2) 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.¹ 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.²

References

Ratni, Hassen; Jodry, Jonathan J.; Lacour, Jérôme; Kündig, E. Peter (2000). "[n-Bu₄N][Δ-TRISPHAT] Salt, an Efficient NMR Chiral Shift Reagent for Neutral Planar Chiral Tricarbonylchromium Complexes". Organometallics. 19 (19): 3997–3999. doi:10.1021/om000437f.
Favarger, France; Goujon-Ginglinger, Catherine; Monchaud, David; Lacour, Jérôme (2004). "Large-Scale Synthesis and Resolution of TRISPHAT [Tris(tetrachlorobenzenediolato) Phosphate(V)] Anion". Journal of Organic Chemistry. 69 (24): 8521–8524. doi:10.1021/jo048641q. PMID 15549835.

[1] Ratni, Hassen; Jodry, Jonathan J.; Lacour, Jérôme; Kündig, E. Peter (2000). "[n-Bu₄N][Δ-TRISPHAT] 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 [Tris(tetrachlorobenzenediolato) Phosphate(V)] Anion". Journal of Organic Chemistry. 69 (24): 8521–8524. doi:10.1021/jo048641q. PMID 15549835.

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