Treatment of tetraaIcohol 1 with glutaroyl (2a, n = 3), adipoyl (2b, n = 4), and pimeloyl (2c, n = 5) dichlorides in the presence of Et(3)N gave the corresponding double-spanned calix[4]resorcarenes 3a-c, in which the insertion of two polymethylene bridges led to the formation of a cavity-shaped architecture resembling a basket. NMR, X-ray, and molecular dynamic-studies showed that one of the two equivalent flattened-cones, which constituted the original cone conformation of 1, had been frozen in the basket derivative. In the solid state the calixarene 3b exists as a supramolecular dimer, in which one of the handles is inserted in the concave cavity of an adjacent molecule. A molecular modeling study revealed that the minimum absolute free energy was associated to the unsymmetrical type of dimer named AB-AC.

B., B., G., D.M., M. C., D.R., C., S., E., B., R., I., et al. (1997). Synthesis of Calix[4]arenes. 5. Design, Synthesis and Computational Studies of Chiral Amidoresorc[4]arenes. JOURNAL OF ORGANIC CHEMISTRY, 62(6), 1788-1794 [10.1021/jo9619692].

Synthesis of Calix[4]arenes. 5. Design, Synthesis and Computational Studies of Chiral Amidoresorc[4]arenes

BOTTA, MAURIZIO;CORELLI, FEDERICO;TAFI, ANDREA;
1997

Abstract

Treatment of tetraaIcohol 1 with glutaroyl (2a, n = 3), adipoyl (2b, n = 4), and pimeloyl (2c, n = 5) dichlorides in the presence of Et(3)N gave the corresponding double-spanned calix[4]resorcarenes 3a-c, in which the insertion of two polymethylene bridges led to the formation of a cavity-shaped architecture resembling a basket. NMR, X-ray, and molecular dynamic-studies showed that one of the two equivalent flattened-cones, which constituted the original cone conformation of 1, had been frozen in the basket derivative. In the solid state the calixarene 3b exists as a supramolecular dimer, in which one of the handles is inserted in the concave cavity of an adjacent molecule. A molecular modeling study revealed that the minimum absolute free energy was associated to the unsymmetrical type of dimer named AB-AC.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11365/43831
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