Electronic and Steric Effects in Binding of Deep Cavitands

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).