Abstract
The observation that per-2,6-O-methyl-3-O-benzoyl-α-cyclodextrin (1) displays some unusual conformational behaviour in solution has led to a detailed investigation by (dynamic) NMR spectroscopy of the equilibration process that occurs in solutions of per-2,3-O-benzoyl-α-cyclodextrin (3) and some related compounds (7–9) between conformational isomers with averagedC 6 andC 3 molecular symmetries in certain organic solvents such as benzene, dichloromethane, and chloroform. The solvent dependence of the conformational equilibrium is also reflected in a spread of values for the specific optical rotations for 3 from +9° in 1,1,2,2-tetrachloroethane, where there is a degenerate equilibrium between species withC 3 molecular symmetry, to +92° in acetone where a species with averagedC 6 symmetry is present.
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This paper is dedicated to the memory of the late Dr C. J. Pedersen.
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Ellwood, P., Spencer, C.M., Spencer, N. et al. Conformational mobility in chemically-modified cyclodextrins. J Incl Phenom Macrocycl Chem 12, 121–150 (1992). https://doi.org/10.1007/BF01053857
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DOI: https://doi.org/10.1007/BF01053857