Triphenylmethyl (also triphenylcarbenium, trityl, or tritylium) hexafluorophosphate is an organic
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...
with the formula or , consisting of the
triphenylmethyl cation and the
hexafluorophosphate anion .
Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to
triphenylmethanol
Triphenylmethanol (also known as triphenylcarbinol, TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions ...
. It is used as a
catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
and
reagent in organic syntheses.
Preparation
Triphenylmethyl hexafluorophosphate can be prepared by combining
silver hexafluorophosphate
Silver hexafluorophosphate, sometimes referred to "silver PF-6," is an inorganic compound with the chemical formula AgPF6.
Uses and reactions
Silver hexafluorophosphate is a commonly encountered reagent in inorganic and organometallic chemistry. ...
with
triphenylmethyl chloride
Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group.
Preparation
Triphenylmethyl chloride is commercially available. ...
:
:AgPF
6 + (C
6H
5)
3CCl → (C
6H
5)
3CPF
6 + AgCl
A second method involves protonolysis of trityl hydroxide:
:HPF
6 + (C
6H
5)
3COH → (C
6H
5)
3CPF
6 + H
2O
Structure and reactions
Triphenylmethyl hexafluorophosphate readily
hydrolyzes
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysi ...
, in a reaction that is the reverse of one of its syntheses:
:(C
6H
5)
3CPF
6 + H
2O → (C
6H
5)
3COH + HPF
6
Triphenylmethyl hexafluorophosphate has been used for abstracting
hydride
In chemistry, a hydride is formally the anion of hydrogen( H−). The term is applied loosely. At one extreme, all compounds containing covalently bound H atoms are called hydrides: water (H2O) is a hydride of oxygen, ammonia is a hydride ...
() 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
The triphenylmethyl radical (often shorted to trityl radical) is an organic compound with the formula (C6H5)3C. It is a persistent radical. It was the first radical ever to be described in organic chemistry. Because of its accessibility, the trit ...
* Triphenylmethane
Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmeth ...
* Triphenylmethanol
Triphenylmethanol (also known as triphenylcarbinol, TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions ...
* Triphenylmethyl chloride
Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group.
Preparation
Triphenylmethyl chloride is commercially available. ...
References
{{Hexafluorophosphates
Aromatic compounds
Carbocations
Hexafluorophosphates
Phenyl compounds