title: Role of the Symmetry of Multipoint Hydrogen Bonding on Chelate Cooperativity in Supramolecular Macrocyclization Processes.
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.
authors.affiliation: Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain).
authors.forename: Carlos
authors.initials: C
authors.lastname: Montoro-García
authors.affiliation: Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain).
authors.forename: Jorge
authors.initials: J
authors.lastname: Camacho-García
authors.affiliation: Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain).
authors.forename: Ana M
authors.initials: AM
authors.lastname: López-Pérez
authors.affiliation: Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain).
authors.forename: María J
authors.initials: MJ
authors.lastname: Mayoral
authors.affiliation: Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain).
authors.forename: Nerea
authors.initials: N
authors.lastname: Bilbao
authors.affiliation: Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain). david.gonzalez.rodriguez@uam.es.
authors.forename: David
authors.initials: D
authors.lastname: González-Rodríguez
keywords: chelate effect; effective molarity; noncovalent synthesis; nucleoside self-assembly; supramolecular chemistry