title: N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors.
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 ≫K2 ≫K3 ≈5>K4, with Ka =5011 m(-1) for 5 in 9:1 CDCl3/[D6]DMSO.
authors.affiliation: Aalto University, School of Science, Department of Applied Physics, Puumiehenkuja 2, 02150, Espoo, Finland. kodiah.beyeh@aalto.fi.|University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, 40014, Jyvaskyla, Finland. kodiah.beyeh@aalto.fi.
authors.forename: N Kodiah
authors.initials: NK
authors.lastname: Beyeh
authors.affiliation: University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, 40014, Jyvaskyla, Finland.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Pan
authors.affiliation: University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, 40014, Jyvaskyla, Finland.
authors.forename: Sandip
authors.initials: S
authors.lastname: Bhowmik
authors.affiliation: University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, 40014, Jyvaskyla, Finland.
authors.forename: Toni
authors.initials: T
authors.lastname: Mäkelä
authors.affiliation: Aalto University, School of Science, Department of Applied Physics, Puumiehenkuja 2, 02150, Espoo, Finland.
authors.forename: Robin H A
authors.initials: RH
authors.lastname: Ras
authors.affiliation: University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, 40014, Jyvaskyla, Finland. kari.t.rissanen@jyu.fi.
authors.forename: Kari
authors.identifier: http://orcid.org/0000-0002-7282-8419
authors.initials: K
authors.lastname: Rissanen
keywords: anions; chlorine; host-guest systems; noncovalent interactions; receptors