bistriflimide

Also known as bistriflylimide anion, Tf2N(-), bistriflimide anion, bistriflimidate, bistriflimide ion, triflimidate, triflimidate ion, bis(trifluoromethane)sulfonimide

Bistriflimide, also known variously as bis(trifluoromethane)sulfonimide, bis(trifluoromethanesulfonyl)imide, bis(trifluoromethanesulfonyl)imidate (and variations thereof), informally and somewhat inaccurately as triflimide or triflimidate, or by the abbreviations TFSI or NTf2, is a non-coordinating anion with the chemical formula [(CF3SO2)2N]−. Its salts are typically referred to as being metal triflimidates.

Chemical data

Formula: C2F6NO4S2-
Molecular weight: 280.15 g/mol
IUPAC name: bis(trifluoromethylsulfonyl)azanide
SMILES: C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F
InChIKey: NHHWJSXMTZIPES-UHFFFAOYSA-N
XLogP: 1.3
Polar surface area: 86 Å²
H-bond donors: 0
H-bond acceptors: 11
Formal charge: -1

via PubChem

Wikidata facts

Subclass of: non-coordinating anion
Has part: nitrogen
Mass: 279.917294

Show 4 more facts

short name: TFSI
Commons category: Bistriflimide anion
canonical SMILES: C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F
chemical formula: C₂F₆NO₄S₂⁻

Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections

Contents

Applications
Bistriflimidic acid
Naming
See also
References

==Applications== The anion is widely used in ionic liquids (such as trioctylmethylammonium bis(trifluoromethylsulfonyl)imide), 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 (LiTFSI) because of its high dissociation and conductivity. It has the added advantage of suppressing crystallinity in poly(ethylene oxide), which increases the conductivity of that polymer below its melting point at 50 °C.

Excerpted from Wikipedia’s “bistriflimide” article, available under the CC BY-SA 4.0 licence.