Anion-Exchange Properties of Trifluoroacetate and Triflate Salts of N-Alkylammonium Resorcinarenes

Fangfang Pan, Ngong Kodiah Beyeh*, Stefania Bertella, Kari Rissanen

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

Abstract

The synthesis of N-benzyl- and N-cyclohexylammonium resorcinarene trifluoroacetate (TFA) and triflate (OTf) salt receptors was investigated. Solid-state analysis by single-crystal X-ray diffraction revealed that the N-alkylammonium resorcinarene salts (NARSs) with different upper substituents had different cavity sizes and different affinities for anions. Anion-exchange experiments by mixing equimolar amounts of N-benzylammonium resorcinarene trifluoroacetate and N-cyclohexylammonium resorcinarene triflate, as well as N-benzylammonium resorcinarene triflate and N-cyclohexylammonium resorcinarene trifluoroacetate showed that the NARS with flexible benzyl groups preferred the larger OTf anion, whereas the rigid cyclohexyl groups preferred the smaller TFA anions. The anion-exchange processes were confirmed in the solid state by single-crystal and powder X-ray diffraction experiments and in the gas phase by electrospray ionization mass spectrometry.

Original languageEnglish
Pages (from-to)782-788
Number of pages7
JournalCHEMISTRY: AN ASIAN JOURNAL
Volume11
Issue number5
DOIs
Publication statusPublished - 4 Mar 2016
MoE publication typeA1 Journal article-refereed

Keywords

  • anion binding
  • crystal engineering
  • host-guest systems
  • macrocycles
  • weak interactions

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