Limits of the Inversion Phenomenon in Triazolyl-Substituted β-Cyclodextrin Dimers
| Autor: | Stéphane Menuel, Frédéric Hapiot, Eric Monflier, Jonathan Potier, Nathalie Azaroual |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
Cyclodextrin 010405 organic chemistry Chemistry Stereochemistry Dimer Organic Chemistry Alkyne 010402 general chemistry 01 natural sciences Inversion (discrete mathematics) Cycloaddition 0104 chemical sciences chemistry.chemical_compound Molecular recognition Azide Physical and Theoretical Chemistry Macromolecule |
| Zdroj: | European Journal of Organic Chemistry. 2014:1547-1556 |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201301681 |
| Popis: | Six different β-cyclodextrin (β-CD) dimers have been synthesized by copper-catalyzed azide alkyne cycloaddition. The nature of the spacer connecting the two β-CDs has been varied in length and hydrophilicity. For each dimer, a detailed NMR study was carried out in D2O. It was found that, whereas β-CD dimers having short spacer exhibited only one conformation, β-CD dimers having long and/or hydrophobic spacers showed two different conformations. Indeed, the latter underwent an inversion process leading to self-inclusion of the spacer in one of the two CD cavities. The behavior of the six β-CD dimers in water has thus been rationalized and this allowed the proportion of “free” cavities actually available for molecular recognition to be determined. |
| Databáze: | OpenAIRE |
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