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

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N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors. / Beyeh, N. Kodiah; Pan, Fangfang; Bhowmik, Sandip; Mäkelä, Toni; Ras, Robin H A; Rissanen, Kari.

In: CHEMISTRY: A EUROPEAN JOURNAL, Vol. 22, No. 4, 22.01.2016, p. 1355-1361.

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Beyeh, N. Kodiah ; Pan, Fangfang ; Bhowmik, Sandip ; Mäkelä, Toni ; Ras, Robin H A ; Rissanen, Kari. / N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors. In: CHEMISTRY: A EUROPEAN JOURNAL. 2016 ; Vol. 22, No. 4. pp. 1355-1361.

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@article{abd3ca3aaafe45e5a57d0fc705546c5c,
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.",
keywords = "anions, chlorine, host-guest systems, noncovalent interactions, receptors",
author = "Beyeh, {N. Kodiah} and Fangfang Pan and Sandip Bhowmik and Toni M{\"a}kel{\"a} and Ras, {Robin H A} and Kari Rissanen",
year = "2016",
month = "1",
day = "22",
doi = "10.1002/chem.201504514",
language = "English",
volume = "22",
pages = "1355--1361",
journal = "CHEMISTRY: A EUROPEAN JOURNAL",
issn = "0947-6539",
number = "4",

}

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TY - JOUR

T1 - N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors

AU - Beyeh, N. Kodiah

AU - Pan, Fangfang

AU - Bhowmik, Sandip

AU - Mäkelä, Toni

AU - Ras, Robin H A

AU - Rissanen, Kari

PY - 2016/1/22

Y1 - 2016/1/22

N2 - 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.

AB - 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.

KW - anions

KW - chlorine

KW - host-guest systems

KW - noncovalent interactions

KW - receptors

UR - http://www.scopus.com/inward/record.url?scp=84954383372&partnerID=8YFLogxK

U2 - 10.1002/chem.201504514

DO - 10.1002/chem.201504514

M3 - Article

VL - 22

SP - 1355

EP - 1361

JO - CHEMISTRY: A EUROPEAN JOURNAL

JF - CHEMISTRY: A EUROPEAN JOURNAL

SN - 0947-6539

IS - 4

ER -

ID: 1436228