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

This is the accepted version of the following article: Angewandte Chemie International Edition 55.1 (2016): 223-227, which has been published in final form at http://dx.doi.org/10.1002/anie.201508854Herein, 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 patternFunding from the European Union (ERC-Starting Grant 279548) and MINECO (CTQ2011-23659 and CTQ2014-57729-P) is gratefully acknowledge