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N ‐Alkyl Ammonium Resorcinarene Salts as High‐Affinity Tetravalent Chloride Receptors
Author(s) -
Beyeh N. Kodiah,
Pan Fangfang,
Bhowmik Sandip,
Mäkelä Toni,
Ras Robin H. A.,
Rissanen Kari
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504514
Subject(s) - resorcinarene , ammonium , alkyl , chemistry , ammonium chloride , chloride , receptor , medicinal chemistry , salt (chemistry) , inorganic chemistry , organic chemistry , biochemistry , molecule
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 K 1 ≫ K 2 ≫ K 3 ≈ 5 > K 4 , with K a =5011 m −1 for 5 in 9:1 CDCl 3 /[D 6 ]DMSO.