Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Selective Binding of Spherical and Linear Anions by Tetraphenyl(thio)urea-Based Dihomooxacalix[4]arene Receptors

Selective Binding of Spherical and Linear Anions by Tetraphenyl(thio)urea-Based Dihomooxacalix[4]arene Receptors
Neal Hickey, Silvano Geremia, Paula M. Marcos, Filipa A. Teixeira, Giovanna Brancatelli, José R. Ascenso
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 1H NMR titrations. Phenylurea 4a displayed a very efficient binding toward the spherical F– and Cl– anions, and the linear CN– (log Kass = 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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01801

DOI: 10.1021/acs.joc.7b01801

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