Molecular modelling study of a dissymmetric calix[4]arene and its methyl ethers
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 2259-2267
- https://doi.org/10.1039/p29940002259
Abstract
A dissymmetric calix[4]arene consisting of four 3,4-dimethylphenol units 1 and its methyl ethers 2–6 have been investigated by applying various force fields as well as by the PM3 semiempirical molecular orbital method. The exploration of the conformational space by random conformational searching has led to numerous local energy minima which differ in the torsion angles around the aryl–methylene bonds. By adjustment of some parameters of the TRIPOS force field a good correspondence could be obtained with experimental data whereas the MM2P force field was not reliable in this respect. Furthermore, a method is proposed for the characterization of calix[4]arenes by a single parameter derived from the torsion angles of the aryl–methylene bonds.Keywords
This publication has 49 references indexed in Scilit:
- Structural features of solid-state calix[4]arene in the cone conformationThe Journal of Organic Chemistry, 1993
- Symbolic representation of the molecular conformation of calixarenesJournal of inclusion phenomena and molecular recognition in chemistry, 1992
- SELECTIVE FUNCTIONALIZATION AND CONFORMATIONAL PROPERTIES OF CALIX[4]ARENES, A REVIEWOrganic Preparations and Procedures International, 1992
- A conformational study of the calixspherand and its complexes with alkalimetal cationsJournal of the Chemical Society, Perkin Transactions 2, 1992
- Stereodynamics of 4,6,10,12,16,18,22,24-octamethylcalix[4]areneThe Journal of Organic Chemistry, 1991
- HAMOG: Molecular graphics program for chemistry 5 biochemistry 5 molecular biology and enzyme researchJournal of Molecular Graphics, 1991
- The development of versions 3 and 4 of the Cambridge Structural Database SystemJournal of Chemical Information and Computer Sciences, 1991
- Thiocalix[4] arenes. I. Synthesis and structure of ethylthiocalix[4]arene methyl ether and the related structure of bromocalix[4]arene methyl etherJournal of inclusion phenomena and molecular recognition in chemistry, 1990
- Crystal and molecular structure of the (1 : 1) clathrate between a calix[4]arene containing onep-nitrophenol unit and tolueneJournal of inclusion phenomena and molecular recognition in chemistry, 1990
- The MMP2 calculational methodJournal of Computational Chemistry, 1987