Amphiphilic properties of synthetic glycolipids based on amide linkages, 4. 13C NMR spectroscopic studies on the gelation of N-octyl-D-gluconamide in aqueous solution

13C NMR measurements were taken on cooling of aqueous solutions of N‐octyl‐D‐gluconamide to follow the process of gelation. On cooling from 90°C gelation sharply occurs at 60–62°C. In the pre‐stage of gelation at 64°C an aggregated species, probably a dimeric form of octylgluconamide, is detected. A...

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Published in:Die Makromolekulare Chemie 1990-12, Vol.191 (12), p.3097-3106
Main Authors: Taravel, François R., Pfannemüller, Beate
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description 13C NMR measurements were taken on cooling of aqueous solutions of N‐octyl‐D‐gluconamide to follow the process of gelation. On cooling from 90°C gelation sharply occurs at 60–62°C. In the pre‐stage of gelation at 64°C an aggregated species, probably a dimeric form of octylgluconamide, is detected. Additional signals for sugar carbons C‐1, C‐4 and C‐6 indicate hydrogen bonding. As a side reaction conversion of the octylgluconamide to the ammonium salt takes place. Assignments of the new signals were made with the ammonium salt formed from D‐gluconamide and the corresponding octylammonium salt of gluconic acid. When the solution of octylgluconamide is kept at 64°C for a longer period, octylgluconamide, free and aggregated, and its ammonium salt coexist. At 64°C relaxation times t1 of the sugar carbons corresponding to the octylgluconamide species are much shorter than those of the salt, indicating a decrease of the mobility of the sugar carbons of the former in the pre‐stage of gelation.
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title Amphiphilic properties of synthetic glycolipids based on amide linkages, 4. 13C NMR spectroscopic studies on the gelation of N-octyl-D-gluconamide in aqueous solution
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