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Electronic and steric effects in binding of deep cavitands.

ABSTRACT: A deep, self-folding cavitand responds to minor electronic differences between suitably sized adamantane guests. Binding constants range from <0.5 to 4000 M(-1) for guests as similar as 1-bromoadamantane and 1-cyanoadamantane. The barriers to guest exchange also vary up to 3 kcal mol(-1).

SUBMITTER: Hooley RJ 

PROVIDER: S-EPMC2765558 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Electronic and steric effects in binding of deep cavitands.

Hooley Richard J RJ   Shenoy Siddhartha R SR   Rebek Julius J  

Organic letters 20081201 23

A deep, self-folding cavitand responds to minor electronic differences between suitably sized adamantane guests. Binding constants range from <0.5 to 4000 M(-1) for guests as similar as 1-bromoadamantane and 1-cyanoadamantane. The barriers to guest exchange also vary up to 3 kcal mol(-1). ...[more]

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