New Watersoluble Macrobicyclic Cavities The watersoluble macrobicyclic compounds 1, 3, 5a, and 5b have been synthesized for the first time bearing large endolipophilic cavities of different sizes and shapes. They were studied with respect to their interactions towards lipophilic guest compounds. The “in/out” isomerism of the hitherto largest endolipophilic cavities 4a, 4b, 5a, and 5b has been investigated by 1H‐, 13C‐NMR spectroscopy and FAB mass spectrometry. The absence of significant 1H‐NMR high‐field shifts in hostguest studies is attributed to the rigidity of cavities 1 and 3, whilst the isomeric cavities 5a and 5b contain very large openings. Orientational fluorescence spectroscopy investigations, however, suggest hostguest interactions of the isomers 5a and 5b with ammonium 8‐anilino‐1‐naphthalenesulfonate (8,1‐ANS).
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Wallon et al. (1990) studied this question.
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