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- W2398481454 abstract "Gluconamides can be easily functionalized to give a variety of compounds that form organogels with a high viscosity. N-n-octyl-d-gluconamide-6-benzoate gelates a large variety of organic solvents, including 1,2-xylene, chloroform, ethyl acetate, and ethanol, to form gels which are, in some cases, stable even above the boiling point of the pure solvent. The 2-methoxy, 6-imidazolyl, 6-acetyl, and 6-cyclohexanoyl derivatives also show gelation, but the 2,4;3,5-dimethylene-protected derivatives do not. Detailed 1H NMR, IR, and X-ray powder diffraction studies reveal that the molecules of most gelators are packed in a head-to-tail fashion. If there is, however, the possibility to form inter-layer hydrogen bonds, as in the case of N-n-octyl-d-gluconamide or N-n-octyl-d-gluconamide-6-(3-pyridyl carboxylate), the molecules are packed head-to-head. Some gluconamides, e.g., those with aliphatic substituents, express their molecular chirality in the supramolecular structures, whereas others, in particular those containing a large aromatic substituent on carbon atom C6, yield nonchiral aggregates, probably due to interfering π−π stacking interactions of the substituents. DSC experiments show that the formation of the gels is an entropy-driven process." @default.
- W2398481454 created "2016-06-24" @default.
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- W2398481454 date "1999-01-01" @default.
- W2398481454 modified "2023-10-16" @default.
- W2398481454 title "Organogels from Carbohydrate Amphiphiles" @default.
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- W2398481454 doi "https://doi.org/10.1021/jo981158t" @default.
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