Enhanced thermodynamic and kinetic stability of calix[4]arene dimers locked in the cone conformation.
作者信息
Vysotsky Myroslav O, Mogck Oliver, Rudzevich Yuliya, Shivanyuk Alexander, Böhmer Volker, Brody Marcus S, Cho Young Lag, Rudkevich Dmitry M, Rebek Julius
机构信息
Abteilung Lehramt Chemie, Fachbereich Chemie und Pharmazie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, D-55099, Mainz, Germany.
出版信息
J Org Chem. 2004 Sep 3;69(18):6115-20. doi: 10.1021/jo049128f.
Wide rim tetraurea derivatives (2a,b) have been prepared from a calix[4]arene rigidified in the cone conformation by two diethyleneglycol ether bridges between adjacent oxygens. In comparison to the analogous tetraurea derivatives (3a,b) of a tetrapentoxy calix[4]arene, 2a,b show an increased thermodynamic stability in mixtures of CDCl(3) and DMSO-d(6). Their kinetic stability as expressed by the rate of guest exchange (benzene or cyclohexane against the solvent benzene-d(6)) is also strongly increased by factors of 30-38. Noticeable differences for the inclusion of selected guests are found.
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