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

Tutkimustuotos: Lehtiartikkeli

Tutkijat

  • N. Kodiah Beyeh
  • Fangfang Pan
  • Sandip Bhowmik
  • Toni Mäkelä
  • Robin Ras

  • Kari Rissanen

Organisaatiot

  • University of Jyväskylä

Kuvaus

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.

Yksityiskohdat

AlkuperäiskieliEnglanti
Sivut1355-1361
Sivumäärä7
JulkaisuCHEMISTRY: A EUROPEAN JOURNAL
Vuosikerta22
Numero4
TilaJulkaistu - 22 tammikuuta 2016
OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

ID: 1436228