Triphenylmethyl hexafluorophosphate
{{chembox
|Watchedfields = changed
|verifiedrevid = 437221912
|ImageFile = Ph3CPF6.png
|ImageSize = 233
|ImageFile2 = Triphenylmethyl-hexafluorophosphate-ion-pair-from-xtal-Mercury-3D-bs.png
|ImageSize2 = 200
|ImageFile3 = Triphenylmethyl-hexafluorophosphate-xtal-packing-Mercury-3D-sf.png
|IUPACName = Triphenylcarbenium hexafluorophosphate
|SystematicName = Diphenylmethylbenzene hexafluoridophosphate
|OtherNames = {{ubl|Triphenylcarbenium hexafluorophosphate(V)|Trityl hexafluorophosphate|Tritylium hexafluorophosphate}}
|Section1 = {{Chembox Identifiers
|CASNo_Ref = {{cascite|correct|??}}
|CASNo = 437-17-2
|ChemSpiderID = 2006130
|EINECS = 207-112-0
|PubChem = 2723954
|SMILES = c1ccc(cc1)[C+](c1ccccc1)c1ccccc1.F[P-](F)(F)(F)(F)F
|StdInChI=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
|StdInChIKey = IBTFOFOFRZKIJU-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|Formula = {{chem2|[(C6H5)3C]+[PF6]−}}
|C=19|H=15|F=6|P=1
|Appearance = Brown powder
|MeltingPtC = 145
}}
|Section7={{Chembox Hazards
|ExternalSDS = [http://www.chemcas.com/material/cas/archive/437-17-2.asp]
|GHSPictograms = {{GHS05}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|314}}
|PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}}
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Triphenylmethyl hexafluorophosphate (also triphenylcarbenium hexafluorophosphate, trityl hexafluorophosphate, or tritylium hexafluorophosphate) is an organic salt with the formula {{chem2|[(C6H5)3C]+[PF6]−}}, consisting of the triphenylcarbenium cation {{chem2|[(C6H5)3C]+}} and the hexafluorophosphate anion {{chem2|[PF6]−}}.{{PubChem|2723954|Triphenylcarbenium hexafluorophosphate}}
Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.{{cite journal |author=Urch, C. |title=Triphenylmethyl Hexafluorophosphate |journal=Encyclopedia of Reagents for Organic Synthesis |year=2001 |doi=10.1002/047084289X.rt363f|isbn=0471936235 }}
Preparation
Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:{{cite journal |last1=Sharp |first1=D. W. A. |last2=Sheppard |first2=N. |title=Complex Fluorides. Part VIII. |journal=Journal of the Chemical Society (Resumed) |date=1957 |pages=674–682 |doi=10.1039/JR9570000674}}
:{{chem2|Ag+[PF6]− + (C6H5)3CCl → [(C6H5)3C]+[PF6]− + AgCl}}
A second method involves protonolysis of triphenylmethanol:{{cite journal |title=Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts |journal=Synthesis |volume=1972 |issue=10 |pages=544 |year=1972 |author1=Olah, G. |author2=Svoboda, J. |author3=Olah, J. |doi= 10.1055/s-1972-21914}}
:{{chem2|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:{{cite journal |author1=Fernandez-Galan, R. |author2=Manzano, B |author3=Otero, A |author4=Lanfranchi, M |author5=Pellinghelli, M. |title=19F and 31P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution |journal=Inorg. Chem. |volume=33 |issue=10 |pages=2309–2312 |year=1994 |doi=10.1021/ic00088a039}}
:{{chem2|[(C6H5)3C]+[PF6]− + H2O → (C6H5)3COH + H[PF6]}}
Triphenylmethyl hexafluorophosphate has been used for abstracting hydride ({{chem|H|-}}) from organic compounds. Treatment of metal-alkene and diene complexes one can generate allyl and pentadienyl complexes, respectively.
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.
See also
References
{{reflist}}
{{Hexafluorophosphates}}