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Restricted motion of guests confined in carceplexes and capsules

TitleRestricted motion of guests confined in carceplexes and capsules
Publication TypeJournal Article
Year of Publication2000
AuthorsChapman, RG, Sherman, JC
JournalJournal of Organic Chemistry
Date PublishedJan
Type of ArticleArticle
ISBN Number0022-3263

Guest orientation within carceplexes and capsules was determined qualitatively from NMR data, and the molecular mobility of guests was determined via coalescence of H-1 NMR signals. Both are highly dependent on guest size and shape, as is interconversion of twistomers. Incarceration of 1,4-thioxane results in a large (1.8 kcal/mol) constraint on thioxane’s conformational mobility (chair-to-chair interconversion). Similar conformational constraints (1.6 kcal/mol) were determined for 1,4-dioxane both when incarcerated in carceplex 1b and when encapsulated reversibly in capsule 3b. Encapsulation-induced conformational constraints of this magnitude are unprecedented, and are particularly striking for the noncovalently linked capsules.

URL<Go to ISI>://000084905400036