Computational studies of calix[4]arene homologs: influence of 5,11,17,23- and 25,26,27,28-substituents on the relative stability of four conformers

Takaaki Harada, Jerzy M. Rudziǹski, Eiji Osawa, Seiji Shinkai

Research output: Contribution to journalArticlepeer-review

64 Citations (Scopus)

Abstract

The effects of 5,11,17,23- and 25,26,27,28-substitutents on the relative stability of four conformers of calix[4]arene are discussed on the basis of a computational method using molecular mechanics (MM3) calculations. It is shown that a substituent in the lower rim site has a decisive role in the determination of the stability order among four conformers of calix[4]arene, while a substituent in the upper rim site only slightly affects the energy differences. It is also shown that in [14]metacyclophanes with no substituent in the lower rim the structure of 1,2-alternate conformers is very different from the typical 1,2-alternate structure common to calix[4]arenes.

Original languageEnglish
Pages (from-to)5941-5954
Number of pages14
JournalTetrahedron
Volume49
Issue number27
DOIs
Publication statusPublished - Jul 2 1993

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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