Publication Type Journal Article
Title Selective Binding of Spherical and Linear Anions by Tetraphenyl(thio)urea-Based Dihomooxacalix[4]arene Receptors
Authors Filipa A. Teixeira Paula M. Marcos José do Rosário Ascenso Giovanna Brancatelli Neal Hickey Silvano Geremia
Groups BioMol
Journal JOURNAL OF ORGANIC CHEMISTRY
Year 2017
Month November
Volume 82
Number 21
Pages 11383-11390
Abstract Three novel tetra(thio)ureido dihomooxacalix[4]arene anion receptors (phenylurea 4a, phenylthiourea 4b, and tert-butylurea 4c) were synthesized and obtained in the cone conformation in solution, as shown by NMR studies. The X-ray crystal structure of 4c is reported. The host guest properties of these receptors toward several anions were investigated by H-1 NMR titrations. Phenylurea 4a displayed a very efficient binding toward the spherical F- and Cl- anions, and the linear CN- (log K-ass = 3.46, 3.50, and 4.02, respectively). In comparison to related bidentate phenylurea dihomooxacalix[4]arenes, tetraphenylurea 4a is more preorganized and the higher number of hydrogen bond donor sites provides a remarkable enhancement of its binding efficiency.
DOI http://dx.doi.org/10.1021/acs.joc.7b01801
ISBN
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Book Title
ISSN 0022-3263
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Conference Name
Bibtex ID ISI:000414724000007
Observations
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