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]−. Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.
Preparation Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:
Ag+[PF6]− + (C6H5)3CCl → [(C6H5)3C]+[PF6]− + AgCl A second method involves protonolysis of triphenylmethanol:
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:
[(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. 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 Triphenylmethyl radical Triphenylcarbenium Triphenylmethane Triphenylmethanol Triphenylmethyl chloride
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