Reverse Anomeric Effect in Large-Amplitude Pyridinium Amide-Containing Mannosyl [2]Rotaxane Molecular Shuttles
| Autor: | Philip Waelès, Frédéric Coutrot, Benjamin Riss-Yaw |
|---|---|
| Přispěvatelé: | Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
crown compounds
Rotaxane Anomeric effect 010405 organic chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Cyclohexane conformation carbohydrates Protonation 010402 general chemistry 01 natural sciences Atomic and Molecular Physics and Optics 0104 chemical sciences chemistry.chemical_compound rotaxanes Molecular shuttle Deprotonation molecular devices chemistry Amide conformation analysis Pyridinium Physical and Theoretical Chemistry |
| Zdroj: | ChemPhysChem ChemPhysChem, Wiley-VCH Verlag, 2016, 17 (12), pp.1860-1869. ⟨10.1002/cphc.201600253⟩ |
| ISSN: | 1439-4235 1439-7641 |
| Popis: | International audience; The reverse anomeric effect (RAE) was investigated in different mannosyl [2]rotaxane molecular shuttle isomers that contain dibenzo-24-crown-8 (DB24C8) as the macrocycle, and anilinium and pyridinium amide as molecular stations. The switching on or off of the RAE was possible depending on both the pyridinium amide motif and the localization of the DB24C8 along the thread. The 1C4 mannopyranosyl chair-like conformation was observed in all the non-interlocked molecules because the anomeric carbon of the mannose is linked to the positively charged nitrogen of the pyridinium unit. In the protonated rotaxanes, the 1C4 chair conformation of the mannose end remains because the DB24C8 resides around the best anilinium station, which is located at the other end of the axle. Upon deprotonation of the anilinium, the DB24C8 shuttles with a large-amplitude motion toward the pyridinium amide stations, where it interacts in a different fashion depending on the pyridinium motif. In one molecular shuttle, the RAE could be switched on or off with control at one end of the encircled thread upon protonation/deprotonation of the other end, through shuttling of the DB24C8. |
| Databáze: | OpenAIRE |
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