(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

Research output: Contribution to journal › Article › Academic › peer-review

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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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