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Triphenylmethyl hexafluorophosphate

Triphenylmethyl hexafluorophosphate
Names
IUPAC name
Triphenylcarbenium hexafluorophosphate
Systematic IUPAC name
Diphenylmethylbenzene hexafluoridophosphate
Other names
  • Triphenylcarbenium hexafluorophosphate(V)
  • Trityl hexafluorophosphate
  • Tritylium hexafluorophosphate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.467 Edit this at Wikidata
EC Number
  • 207-112-0
  • InChI=1S/C19H15.F6P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-7(2,3,4,5)6/h1-15H;/q+1;-1
    Key: IBTFOFOFRZKIJU-UHFFFAOYSA-N
  • c1ccc(cc1)[C+](c1ccccc1)c1ccccc1.F[P-](F)(F)(F)(F)F
Properties
[(C6H5)3C]+[PF6]−
Molar mass 388.293 g·mol−1
Appearance Brown powder
Melting point 145 °C (293 °F; 418 K)
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Safety data sheet (SDS) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triphenylmethyl hexafluorophosphate (also triphenylcarbenium hexafluorophosphate, trityl hexafluorophosphate, or tritylium hexafluorophosphate) is an organic salt with the formula [(C6H5)3C]+[PF6]−, consisting of the triphenylcarbenium cation [(C6H5)3C]+ and the hexafluorophosphate anion [PF6]−.[1]

Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.[2]

Preparation

Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:[3]

Ag+[PF6]− + (C6H5)3CCl → [(C6H5)3C]+[PF6]− + AgCl

A second method involves protonolysis of triphenylmethanol:[4]

H[PF6] + (C6H5)3COH → [(C6H5)3C]+[PF6]− + H2O

Structure and reactions

Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses:[5]

[(C6H5)3C]+[PF6]− + H2O → (C6H5)3COH + H[PF6]

Triphenylmethyl hexafluorophosphate has been used for abstracting hydride (H−
) from organic compounds. Treatment of metal-alkene and diene complexes one can generate allyl and pentadienyl complexes, respectively.[2]

Triphenylmethyl perchlorate is a common substitute for triphenylmethyl hexafluorophosphate. However, the perchlorate is not used as widely, because, like other organic perchlorates, it is potentially explosive.[2]

See also

References

  1. ^ Triphenylcarbenium hexafluorophosphate from PubChem
  2. ^ a b c Urch, C. (2001). "Triphenylmethyl Hexafluorophosphate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt363f. ISBN 0471936235.
  3. ^ Sharp, D. W. A.; Sheppard, N. (1957). "Complex Fluorides. Part VIII". Journal of the Chemical Society (Resumed): 674–682. doi:10.1039/JR9570000674.
  4. ^ Olah, G.; Svoboda, J.; Olah, J. (1972). "Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts". Synthesis. 1972 (10): 544. doi:10.1055/s-1972-21914.
  5. ^ Fernandez-Galan, R.; Manzano, B; Otero, A; Lanfranchi, M; Pellinghelli, M. (1994). "19F and 31P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution". Inorg. Chem. 33 (10): 2309–2312. doi:10.1021/ic00088a039.
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