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Role of the Symmetry of Multipoint Hydrogen Bonding on Chelate Cooperativity in Supramolecular Macrocyclization Processes
Author(s) -
MontoroGarcía Carlos,
CamachoGarcía Jorge,
LópezPérez Ana M.,
Mayoral María J.,
Bilbao Nerea,
GonzálezRodríguez David
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508854
Subject(s) - cooperativity , supramolecular chemistry , hydrogen bond , chelation , symmetry (geometry) , chemistry , crystallography , chemical physics , molecule , inorganic chemistry , crystal structure , mathematics , organic chemistry , biochemistry , geometry
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.