Enhanced thermodynamic and kinetic stability of calix[4]arene dimers locked in the cone conformation

The Journal of Organic Chemistry
M O VysotskyJ Rebek

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 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.

References

Dec 19, 1995·Proceedings of the National Academy of Sciences of the United States of America·K D Shimizu, J Rebek
Jan 10, 2001·The Journal of Organic Chemistry·A ArduiniA Pochini
Jul 17, 2003·Chemistry : a European Journal·Myroslav O VysotskyVolker Böhmer
Jun 1, 1999·Angewandte Chemie·Marcus S BrodyJulius Rebek

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Citations

Mar 2, 2012·Inorganic Chemistry·Peter D FrischmannMark J MacLachlan
Jul 26, 2005·Chemical Communications : Chem Comm·Lan HeBing Gong
Jul 13, 2006·Chemical Communications : Chem Comm·Anca BogdanVolker Böhmer
May 14, 2008·Chemical Communications : Chem Comm·Anthony W ColemanJohn A Ripmeester
Jul 13, 2006·Proceedings of the National Academy of Sciences of the United States of America·Lan HeBing Gong
Dec 6, 2006·Angewandte Chemie·Dariush AjamiJulius Rebek
Mar 11, 2008·Organic & Biomolecular Chemistry·Ivan VatsouroVolker Böhmer
Apr 11, 2009·Angewandte Chemie·Yuliya RudzevichVolker Böhmer
Mar 17, 2010·Chemistry : a European Journal·Yuliya RudzevichVolker Böhmer
Oct 27, 2004·Organic & Biomolecular Chemistry·Yuliya RudzevichIris Thondorf
Jul 4, 2013·Organic & Biomolecular Chemistry·Juliana Baptista SimõesSergio Antonio Fernandes
Dec 25, 2007·The Journal of Organic Chemistry·Damien BraekersJean F Desreux
Jan 20, 2009·Organic Letters·Mingwei GengBing Gong
Mar 9, 2007·Organic Letters·Ivan VatsouroVolker Böhmer
Feb 12, 2005·Organic Letters·Yuliya RudzevichVolker Böhmer

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