Bistriflimide


Bistriflimide, systematically known as bissulfonimide and colloquially as TFSI, is a non-coordinating anion with the chemical formula −. Its salts are typically referred to as being metal triflimidates.

Applications

The anion is widely used in ionic liquids, since it is less toxic and more stable than more "traditional" counterions such as tetrafluoroborate.
This anion is also of importance in lithium-ion and lithium metal batteries because of its high dissociation and conductivity. It has the added advantage of suppressing crystallinity in poly, which increases the conductivity of that polymer below its melting point at 50 °C.

Triflimidic acid

The conjugate acid of bistriflimide, which is frequently referred to by the trivial name triflimidic acid, is a commercially available superacid. It is a crystalline compound, but is hygroscopic to the point of being deliquescent. Owing to its very high acidity and good compatibility with organic solvents it has been employed as a catalyst in a wide range of chemical reactions.
Its pKa value in water cannot be accurately determined but in acetonitrile it has been estimated as −0.10 and in 1,2-dichloroethane −12.3, making it more acidic than triflic acid.

Naming

Developing an IUPAC name for bistriflimide that indicates the structure and reactivity is challenging, and changes to current names have been proposed. The main difficulty arises from the ambiguous use of the word amide to mean an acylated amine or the anionic form of an amine. Likewise, imide can refer to a bisacylated amine or a twice deprotonated amine. Thus, depending on the system used, there is ambiguity as to whether amide or imide is being used to refer to the parent acid or the anion. The complications in naming these compounds was highlighted in an article by the IUPAC. Since then, the IUPAC has recommended that derivatives of anionic nitrogen can be named as azanides, so bisazanide would be an acceptable and unambiguous name for bistriflimide anion. The parent acid, whose trivial name is triflimidic acid, would then be called bisazane.