Rigid cone calix[4]arenes as π-donor systems: complexation of organic molecules and ammonium ions in organic media
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 839-846
- https://doi.org/10.1039/p29960000839
Abstract
One step synthesis of calix[4]arene biscrowns, with a rigid cone structure and alkyl or phenyl groups at the ‘upper rim’, has been performed. The binding ability of these rigidified cone calix[4]arenes 1–4,13 has been evaluated, in apolar organic media, towards neutral organic molecules and ammonium cation salts. Comparison with more flexible analogues 5,6,11 shows that only rigid cone calix[4]arenes are able to complex organic species. The association constants strongly depend on the type of substituents present at the upper rim. The X-ray crystal structure of the endo complex p-cyclohexyl-25,26-27,28-biscrown-3-calix[4]arene 3 with CH3NO2 has been resolved.Keywords
This publication has 69 references indexed in Scilit:
- Hydrogen-Bonding: An UpdateCrystallography Reviews, 1995
- Molecular dynamics study of p-tert-butylcalix[4]arenetetraamide and its complexes with neutral and cationic guests. Influence of solvation on structures and stabilitiesJournal of the American Chemical Society, 1993
- New artificial receptors from selectively functionalized calix[4]arenesSupramolecular Chemistry, 1993
- Symbolic representation of the molecular conformation of calixarenesJournal of inclusion phenomena and molecular recognition in chemistry, 1992
- An introduction to NMR titration for studying rapid reversible complexationJournal of Chemical Education, 1992
- Direct synthesis of calix[4]arenes with two different phenolic units in alternating orderThe Journal of Organic Chemistry, 1992
- Novel Strategies for the Complexation of Neutral Guest Molecules by Synthetic Macrocyclic HostsJournal of Coordination Chemistry, 1988
- Binding of acetylcholine and other molecular cations by a macrocyclic receptor molecule of speleand typeJournal of the Chemical Society, Chemical Communications, 1984
- Nuclear Magnetic Resonance Study of Proton Exchange Involving Ion Pairs of Ammonium Salts in t-Butyl AlcoholJournal of the American Chemical Society, 1966
- 56. The conductance of solutions in which the solvent molecule is “large.” Part VII. Solutions in triaryl phosphitesJournal of the Chemical Society, 1961