Study of CH/π Interactions in the Molecular Recognition between Acetyl Galactopyranoside and 6-substituted 2-Methoxypyridines and 2(1H)-Pyridones
| Autor: | Fabián Cuétara-Guadarrama, Karla Ramírez-Gualito, Gabriel Cuevas |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry Intermolecular force Supramolecular chemistry Glycoside Affinity constant General Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences Molecular recognition chemistry Non-covalent interactions Titration |
| Zdroj: | Journal of the Mexican Chemical Society. 61 |
| ISSN: | 2594-0317 1870-249X |
| DOI: | 10.29356/jmcs.v61i3.346 |
| Popis: | A series of 6-substituted 2-methoxypyridine and 2(1H)-pyridones was designed and synthesized for its evaluation in the molecular recognition of acetyl 2,3,4,6-tetra-O-methyl-b-D-galactopyranoside substrate. 1H-NMR titration (affinity constant Ka determination) and chemical shift perturbation experiments were performed to evaluate the capacity of these receptors to form CH/π interactions with the substrate. The addition of 2-methoxypyridines to the substrate effected up-field shift for the H3, H4 and H5 proton signals and down-field shift for the H2 proton signal of galactopyranoside substrate. The determined affinity constant Ka values for the association between 2(1H)-pyridones and galactopyranoside showed that molecular recognition was weak. These results have demonstrated the existence of weak CH/π interactions and have reflected their weak intermolecular nature. Finally DFT calculations were performed to illustrate the geometry of the molecular recognition between 2(1H)-pyridones and galactopyranoside. |
| Databáze: | OpenAIRE |
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