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Chemistry · L5 · Preorganization & the Macrocyclic Effect

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Contrasts a flexible acyclic ligand with a rigid, pre-shaped macrocyclic host to show how preorganization lowers the entropic cost of guest binding and drives the macrocyclic effect.

by @openstemUpdated Chemistry
Host designMust fold around guest:large conformational entropy lossBinding sites alreadyaligned to the guestBinding pays anentropy penalty: weaker complexMinimal reorganization needed:stronger complex — macrocyclic effectGuest held looselyGuest held tightlye.g. cryptand > crown ether > open-chain glymeFlexible acyclic chain of donor atomsRigid macrocycle: pre-shaped cavity

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