4.8 Article

Electronic and Steric Effects in Binding of Deep Cavitands

Journal

ORGANIC LETTERS
Volume 10, Issue 23, Pages 5397-5400

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol8022775

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Funding

  1. Skaggs Institute
  2. National Institutes of Health [GM27932]

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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).

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