An attempt to synthesize the two monomers of CDTOH: Unexpected NMR and X-ray diffraction crystal analysis
Résumé
Two monomer compounds of CDTOH, 6 A-deoxy-6 A-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)-per-O-methylated β-cyclodextrin 4 and 6 A-deoxy-6 A-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl) β-cyclodextrin 7, have been synthesized via click chemistry. The structures were confirmed by 1 H NMR, 13 C NMR and ESI-HRMS. In comparison to the 1 H NMR spectra of compound 4 and intermediate 6, two sets of peaks in the high field of 7 are somewhat unusual. The X-ray single-crystal analysis of 7 showed the existence of an intramolecular hydrogen bond between the CH 2 OH donor of glucose B and the terminal hydroxy acceptor of the side chain, leading to the 4-(2-hydroxyethyl)-1H-1,2,3-triazole group protruding outside the cavity and embedding in the hydrophobic cavity of the adjacent molecule (interinclusion) to form an interlocked helical columnar superstructure.
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