(Thio)urea resorcinarene cavitands: Complexation and membrane transport of halide anions

Harold Boerrigter; Lennart Grave; J. Willem M. Nissink; Lysander A.J. Chrisstoffels; John H. van der Maas; Willem Verboom; Feike de Jong; David N. Reinhoudt

doi:10.1021/jo972127l

(Thio)urea resorcinarene cavitands: Complexation and membrane transport of halide anions

Harold Boerrigter, Lennart Grave, J. Willem M. Nissink, Lysander A.J. Chrisstoffels, John H. van der Maas, Willem Verboom, Feike de Jong, David N. Reinhoudt

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Abstract

Reaction of aminomethylcavitands with iso(thio)cyanates gives (thio)urea-functionalized resorcinarene cavitands, which represent a novel class of neutral anion receptors. The complexation of halide anions has been studied both with infrared and ¹H NMR spectroscopy. The receptors have a small preference for chloride over the other halides; p-fluorophenylthiourea cavitand 8a gives the highest association constant (K_ass = 4.7 × 10⁵ M^-1 with chloride in CDCl₃). A cooperative effect of the ligating (thio)urea moieties is indicated by the lower affinity of the corresponding tris(thio)urea-functionalized cavitands. For the first time facilitated membrane transport of halide anions through supported liquid membranes is achieved.

Original language	English
Pages (from-to)	4174-4180
Journal	The journal of organic chemistry
Volume	63
Issue number	13
DOIs	https://doi.org/10.1021/jo972127l
Publication status	Published - 1998

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@article{892924d0583646a7b05765d8cc0e6263,

title = "(Thio)urea resorcinarene cavitands: Complexation and membrane transport of halide anions",

abstract = "Reaction of aminomethylcavitands with iso(thio)cyanates gives (thio)urea-functionalized resorcinarene cavitands, which represent a novel class of neutral anion receptors. The complexation of halide anions has been studied both with infrared and 1H NMR spectroscopy. The receptors have a small preference for chloride over the other halides; p-fluorophenylthiourea cavitand 8a gives the highest association constant (Kass = 4.7 × 105 M-1 with chloride in CDCl3). A cooperative effect of the ligating (thio)urea moieties is indicated by the lower affinity of the corresponding tris(thio)urea-functionalized cavitands. For the first time facilitated membrane transport of halide anions through supported liquid membranes is achieved.",

author = "Harold Boerrigter and Lennart Grave and Nissink, {J. Willem M.} and Chrisstoffels, {Lysander A.J.} and {van der Maas}, {John H.} and Willem Verboom and {de Jong}, Feike and Reinhoudt, {David N.}",

year = "1998",

doi = "10.1021/jo972127l",

language = "English",

volume = "63",

pages = "4174--4180",

journal = "The journal of organic chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - (Thio)urea resorcinarene cavitands

T2 - Complexation and membrane transport of halide anions

AU - Boerrigter, Harold

AU - Grave, Lennart

AU - Nissink, J. Willem M.

AU - Chrisstoffels, Lysander A.J.

AU - van der Maas, John H.

AU - Verboom, Willem

AU - de Jong, Feike

AU - Reinhoudt, David N.

PY - 1998

Y1 - 1998

N2 - Reaction of aminomethylcavitands with iso(thio)cyanates gives (thio)urea-functionalized resorcinarene cavitands, which represent a novel class of neutral anion receptors. The complexation of halide anions has been studied both with infrared and 1H NMR spectroscopy. The receptors have a small preference for chloride over the other halides; p-fluorophenylthiourea cavitand 8a gives the highest association constant (Kass = 4.7 × 105 M-1 with chloride in CDCl3). A cooperative effect of the ligating (thio)urea moieties is indicated by the lower affinity of the corresponding tris(thio)urea-functionalized cavitands. For the first time facilitated membrane transport of halide anions through supported liquid membranes is achieved.

AB - Reaction of aminomethylcavitands with iso(thio)cyanates gives (thio)urea-functionalized resorcinarene cavitands, which represent a novel class of neutral anion receptors. The complexation of halide anions has been studied both with infrared and 1H NMR spectroscopy. The receptors have a small preference for chloride over the other halides; p-fluorophenylthiourea cavitand 8a gives the highest association constant (Kass = 4.7 × 105 M-1 with chloride in CDCl3). A cooperative effect of the ligating (thio)urea moieties is indicated by the lower affinity of the corresponding tris(thio)urea-functionalized cavitands. For the first time facilitated membrane transport of halide anions through supported liquid membranes is achieved.

U2 - 10.1021/jo972127l

DO - 10.1021/jo972127l

M3 - Article

SN - 0022-3263

VL - 63

SP - 4174

EP - 4180

JO - The journal of organic chemistry

JF - The journal of organic chemistry

IS - 13

ER -

(Thio)urea resorcinarene cavitands: Complexation and membrane transport of halide anions

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