N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf2]–) and Tris(trifluoromethanesulfonyl)methide ([CTf3]–) Salts: Synthesis and Characterization

Katarina M. Johansson; Josefina Adebahr; Patrick C. Howlett; Maria Forsyth; Douglas R. MacFarlane

doi:10.1071/CH06299

RESEARCH FRONT

N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf₂]^–) and Tris(trifluoromethanesulfonyl)methide ([CTf₃]^–) Salts: Synthesis and Characterization

Katarina M. Johansson ^A ^C , Josefina Adebahr ^B , Patrick C. Howlett ^B , Maria Forsyth ^B and Douglas R. MacFarlane ^A

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Monash University, Clayton VIC 3800, Australia.

^B Department of Materials Engineering, Monash University, Clayton VIC 3800, Australia.

^C Corresponding author. Email: katarina.johansson@sci.monash.edu.au

Australian Journal of Chemistry 60(1) 57-63 https://doi.org/10.1071/CH06299
Submitted: 17 August 2006 Accepted: 12 October 2006 Published: 29 January 2007

Abstract

Novel salts based the pyrrolidinium cation [C_nmpyr]⁺ (where n denote the number of carbons in the straight alkyl chain) and either the [NPf₂]^– or [CTf₃]^– anions have been synthesized and characterized to determine their thermal behaviour, stability, and conductivity. [C₁mpyr][NPf₂], [C₂mpyr][NPf₂], and [C₁mpyr][CTf₃] exhibit behaviour indicative of a plastic crystal phase. Both [C₃mpyr][NPf₂] and [C₄mpyr][NPf₂] are RTILs, while all of the [CTf₃]^– salts, have melting points above 60°C. [C₃mpyr][NPf₂] exhibited the widest electrochemical window of 5.5 V. The [NPf₂]^– salt exhibited similar reductive limits to the [NTf₂]^– anion, –3.2 V versus Fc⁺|Fc, while [CTf₃]^– had lower reductive stability. The [CTf₃]^– salts were more stable towards oxidation, +2.5 V versus Fc⁺|Fc, compared to the [NPf₂]^– and [NTf₂]^– salts.

References

^A This compound is frequently described as an ‘imide’ in the materials literature but more accurately, and consistently with related compounds, as an ‘amide’ in the chemical literature.

N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf2]–) and Tris(trifluoromethanesulfonyl)methide ([CTf3]–) Salts: Synthesis and Characterization

Abstract

Subscriber Login

N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf₂]^–) and Tris(trifluoromethanesulfonyl)methide ([CTf₃]^–) Salts: Synthesis and Characterization