Insight into the reaction between a primary amine and a cavitand with an introverted aldehyde group: an enzyme-like mechanism.

Density functional theory investigations reveal that a cavitand with an introverted aldehyde group not only provides the host-guest interaction for preorganizing the substrate and stabilizing the hemiaminal intermediate, but also acts as an acid/base catalyst in the subsequent dehydration step in its reaction with a primary amine.