6533b825fe1ef96bd1282981

RESEARCH PRODUCT

Enhanced thermodynamic and kinetic stability of calix[4]arene dimers locked in the cone conformation.

Dmitry M. RudkevichVolker BöhmerJulius RebekMyroslav O. VysotskyYoung Lag ChoMarcus S. BrodyOliver MogckYuliya RudzevichAlexander Shivanyuk

subject

Magnetic Resonance SpectroscopyCyclohexaneMolecular StructureStereochemistryDimerOrganic ChemistryMolecular ConformationEtherInclusion compoundSolventchemistry.chemical_compoundCrystallographyKineticschemistryPhenolsCalixareneThermodynamicsUreaChemical stabilityCalixarenesBenzene

description

Wide rim tetraurea derivatives (2a,b) have been prepared from a calix[4]arene rigidified in the cone conformation by two diethyleneglycol ether bridges between adjacent oxygens. In comparison to the analogous tetraurea derivatives (3a,b) of a tetrapentoxy calix[4]arene, 2a,b show an increased thermodynamic stability in mixtures of CDCl(3) and DMSO-d(6). Their kinetic stability as expressed by the rate of guest exchange (benzene or cyclohexane against the solvent benzene-d(6)) is also strongly increased by factors of 30-38. Noticeable differences for the inclusion of selected guests are found.

yearjournalcountryeditionlanguage
2004-09-18The Journal of organic chemistry
10.1021/jo049128fhttps://pubmed.ncbi.nlm.nih.gov/15373497