Enhanced Thermodynamic and Kinetic Stability of Calix[4]arene Dimers Locked in the Cone Conformation
- 12 August 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (18) , 6115-6120
Abstract
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 CDCl3 and DMSO-d6. Their kinetic stability as expressed by the rate of guest exchange (benzene or cyclohexane against the solvent benzene-d6) is also strongly increased by factors of 30−38. Noticeable differences for the inclusion of selected guests are found.Keywords
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