Role of the Symmetry of Multipoint Hydrogen Bonding on Chelate Cooperativity in Supramolecular Macrocyclization Processes

Abstract

Abstract Herein, we analyze the intrinsic chelate effect that multipoint H‐bonding patterns exert on the overall energy of dinucleoside cyclic systems. Our results indicate that the chelate effect is regulated by the symmetry of the H‐bonding pattern, and that the effective molarity is reduced by about three orders of magnitude when going from the unsymmetric ADD–DAA or DDA–AAD patterns to the symmetric DAD–ADA pattern.