Ion-Pair Recognition of Tetramethylammonium Salts by Halogenated Resorcinarenes

Research output: Contribution to journalArticleScientificpeer-review

Researchers

  • Ngong Kodiah Beyeh
  • Dominik P. Weimann
  • Lena Kaufmann
  • Christoph A. Schalley
  • Kari Rissanen

Research units

  • University of Jyväskylä
  • Free University of Berlin

Abstract

The non-covalent interactions of different upper-rim-substituted C2-resorcinarenes with tetramethylammonium salts were analyzed in the gas phase in an Electrospray Ionization Fourier-transform ion-cyclotron-resonance (ESI-FTICR) mass spectrometer and by 1H NMR titrations. The order of binding strengths of the hosts towards the tetramethylammonium cation in the gas phase reflects the electronic nature of the substituents on the upper rim of the resorcinarene. In solution, however, a different trend with particularly high binding constants for halogenated resorcinarenes has been observed. This trend can be explained by a synergetic effect originating from the interaction of the halogenated resorcinarenes with the counter anions through hydrogen bonding. This study highlights the importance of weak interactions in recognition processes and points out the benefits of comparing the gas-phase data with results obtained from solution experiments.

Details

Original languageEnglish
Pages (from-to)5552–5557
JournalCHEMISTRY: A EUROPEAN JOURNAL
Volume18
Issue number18
Publication statusPublished - Apr 2012
MoE publication typeA1 Journal article-refereed

ID: 11468054