Synthesis of C-Alkylcalix[4]arenes. 5. Design, Synthesis, Computational Studies, and Homodimerization of Polymethylene-Bridged Resorc[4]arenes

Bruno Botta, Giuliano Delle Monache, Maria Cristina De Rosa, Catia Seri, Ettore Benedetti, Rosa Iacovino, Maurizio Botta, Federico Corelli, Vega Masignani, Andrea Tafi, Eszter Gacs-Baitz, Antonello Santini, Domenico Misiti

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Treatment of tetraalcohol 1 with glutaroyl (2a, n = 3), adipoyl (2b, n = 4), and pimeloyl (2c, n = 5) dichlorides in the presence of Et 3N 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.

Original languageEnglish
Pages (from-to)1788-1794
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number6
Publication statusPublished - Dec 1 1997

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Botta, B., Monache, G. D., De Rosa, M. C., Seri, C., Benedetti, E., Iacovino, R., Botta, M., Corelli, F., Masignani, V., Tafi, A., Gacs-Baitz, E., Santini, A., & Misiti, D. (1997). Synthesis of C-Alkylcalix[4]arenes. 5. Design, Synthesis, Computational Studies, and Homodimerization of Polymethylene-Bridged Resorc[4]arenes. Journal of Organic Chemistry, 62(6), 1788-1794.