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Triphenylmethyl hexafluorophosphate

Chemical compound From Wikipedia, the free encyclopedia

Triphenylmethyl hexafluorophosphate
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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]

Quick facts Names, Identifiers ...

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

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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]

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See also

References

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