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Triflidic acid (IUPAC name: tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf 3 CH) is an organic superacid.It is one of the strongest known carbon acids and is among the strongest Brønsted acids in general, with an acidity exceeded only by the carborane acids.
The first to investigate trifluoromethyl groups in relationship to biological activity was F. Lehmann in 1927. [5] An early review appeared in 1958. [6] An early synthetic method was developed by Frédéric Swarts in 1892, [7] based on antimony fluoride. In this reaction benzotrichloride was reacted with SbF 3 to form PhCF 2 Cl and PhCF 3.
In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula R−OSO 2 CF 3 and structure R−O−S(=O) 2 −CF 3. The triflate group is often represented by −OTf, as opposed to −Tf, which is the triflyl group, R−SO 2 CF 3. For example, n-butyl triflate can be written as CH 3 CH 2 CH ...
Trifluoromethyl group covalently bonded to an R group. The trifluoromethyl group is a functional group that has the formula-CF 3.The naming of is group is derived from the methyl group (which has the formula -CH 3), by replacing each hydrogen atom by a fluorine atom.
In organic chemistry, the triflyl group (systematic name: trifluoromethanesulfonyl group) is a functional group with the formula R−SO 2 CF 3 and structure R−S(=O) 2 −CF 3. The triflyl group is often represented by –Tf. The related triflate group (trifluoromethanesulfonate) has the formula R−OSO 2 CF 3, and is represented by –OTf. [1]
Its pK a value in water cannot be accurately determined but in acetonitrile it has been estimated as −0.10 and in 1,2-dichloroethane −12.3 (relative to the pK a value of 2,4,6-trinitrophenol (picric acid), anchored to zero to crudely approximate the aqueous pK a scale [2]), making it more acidic than triflic acid (pK a MeCN = 0.70, pK a DCE ...
Triflic anhydride is prepared by dehydration of triflic acid using P 4 O 10. [2] Triflic anhydride is useful for converting ketones into enol triflates. [4] In a representative application, is used to convert an imine into a NTf group. [5] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond. [6] [7]
It is also used as an acidic titrant in nonaqueous acid-base titration because it behaves as a strong acid in many solvents (acetonitrile, acetic acid, etc.) where common mineral acids (such as HCl or H 2 SO 4) are only moderately strong. With a K a = 5 × 10 14, pK a = −14.7 ± 2.0, [1] triflic acid qualifies as a superacid. It owes many of ...