N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors

N. Kodiah Beyeh*, Fangfang Pan, Sandip Bhowmik, Toni Mäkelä, Robin H A Ras, Kari Rissanen

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

Abstract

N-Alkyl ammonium resorcinarene salts (NARYs, Y=triflate, picrate, nitrate, trifluoroacetates and NARBr) as tetravalent receptors, are shown to have a strong affinity for chlorides. The high affinity for chlorides was confirmed from a multitude of exchange experiments in solution (NMR and UV/Vis), gas phase (mass spectrometry), and solid-state (X-ray crystallography). A new tetra-iodide resorcinarene salt (NARI) was isolated and fully characterized from exchange experiments in the solid-state. Competition experiments with a known monovalent bis-urea receptor (5) with strong affinity for chloride, reveals these receptors to have a much higher affinity for the first two chlorides, a similar affinity as 5 for the third chloride, and lower affinity for the fourth chloride. The receptors affinity toward chloride follows the trend K1蠑K2蠑K3≈5>K4, with Ka=5011 m-1 for 5 in 9:1 CDCl3/[D6]DMSO. Completing the circle: N-Alkyl ammonium resorcinarene salts (NARYs) are high-affinity tetravalent chloride receptors. Competition experiments including multiple 1H NMR titration experiments reveal that NARYs have a higher affinity towards the first two Cl- ions, comparable affinity for the third Cl-, and lower affinity for the fourth Cl- compared to a known bis-urea receptor.

Original languageEnglish
Pages (from-to)1355-1361
Number of pages7
JournalCHEMISTRY: A EUROPEAN JOURNAL
Volume22
Issue number4
DOIs
Publication statusPublished - 22 Jan 2016
MoE publication typeA1 Journal article-refereed

Keywords

  • anions
  • chlorine
  • host-guest systems
  • noncovalent interactions
  • receptors

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  • Datasets

    CCDC 1429824: Experimental Crystal Structure Determination

    Beyeh, N. (Creator), Bhowmik, S. (Contributor), Mäkelä, T. (Contributor), Pan, F. (Contributor), Ras, R. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2016

    Dataset

    CCDC 1429822: Experimental Crystal Structure Determination

    Beyeh, N. (Contributor), Bhowmik, S. (Contributor), Mäkelä, T. (Contributor), Pan, F. (Contributor), Ras, R. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2016

    Dataset

    CCDC 1429823: Experimental Crystal Structure Determination

    Beyeh, N. (Creator), Bhowmik, S. (Contributor), Mäkelä, T. (Contributor), Pan, F. (Contributor), Ras, R. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2016

    Dataset

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