Triphenylmethyl hexafluorophosphate

Triphenylmethyl hexafluorophosphate is an organic salt with the formula C
19H
15F
6P or (C
6H
5)
3CPF
6, consisting of the triphenylmethyl cation [(C
6H
5)
3C]+
 and the hexafluorophosphate anion] [PF
6]−
. The cation is also called triphenylcarbenium, trityl cation, or tritylium.[1]

Triphenylmethyl hexafluorophosphate
Names
Other names
Trityl hexafluorophosphate
Triphenylcarbenium hexafluorophosphate
Tritylium hexafluorophosphate
Diphenylmethylbenzene hexafluorophosphate (IUPAC)
Identifiers
3D model (JSmol)
ECHA InfoCard 100.006.467
Properties
C19H15F6P
Molar mass 388.31 g/mol
Appearance brown powder
Melting point 145 °C (293 °F; 418 K)
Hazards
Safety data sheet
R-phrases (outdated) R34, R26, R36/37, R39, R45
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

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]

AgPF6 + (C6H5)3CCl → (C6H5)3CPF6 + AgCl

A second method involves protonolysis of generating triphenylmethanol :[4]

HPF6 + (C6H5)3COH → (C6H5)3CPF6 + H2O

Structure and reactions

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

(C6H5)3CPF6 + H2O → (C6H5)3COH + HPF6

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. U. S. National Institutes of Health (2019) "PubChem ID 2723954 - Triphenylcarbenium hexafluorophosphate". Entry in NCBI's PubChem database, accessed on 2019-07-25.
  2. Urch, C. (2001). "Triphenylmethyl Hexafluorophosphate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt363f. ISBN 0471936235.
  3. Sharp, D., Shepard, N. (1956). "Complex Fluorides. Part VIII". University Chemical Laboratory, Cambridge: 674–682.CS1 maint: multiple names: authors list (link)
  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.CS1 maint: multiple names: authors list (link)
  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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