(Thio)urea Resorcinarene Cavitands. Complexation and Membrane Transport of Halide Anions

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 prefere...

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Published inJournal of organic chemistry Vol. 63; no. 13; pp. 4174 - 4180
Main Authors Boerrigter, Harold, Grave, Lennart, Nissink, J. Willem M, Chrisstoffels, Lysander A. J, van der Maas, John H, Verboom, Willem, de Jong, Feike, Reinhoudt, David N
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.06.1998
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUPPORTED LIQUID MEMBRANES
CONSTANTS
SOLVENTS
MOLECULAR RECOGNITION
CROWN ETHERS
X-RAY STRUCTURE
NEUTRAL RECEPTORS
PROTON
UREA
CARRIER
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Summary: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.
Bibliography:ark:/67375/TPS-MNG97T5B-N
istex:FD1845966D36ED64AAC5B9769F1BE3895D450CCC
ISSN:0022-3263
1520-6904
DOI:10.1021/jo972127l