G‑Arylated Hydrogen-Bonded Cyclic Tetramer Assemblies with Remarkable Thermodynamic and Kinetic Stability

The preparation and self-assembly of novel G–C dinucleoside monomers that are equipped with electron-poor aryl groups at the G-N 2 amino group have been studied. Such monomers associate via Watson–Crick H-bonding into discrete unstrained tetrameric macrocycles that arise as a thermodynamically and k...

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Bibliographic Details
Published in:Organic letters 2015-06, Vol.17 (11), p.2664-2667
Main Authors: Romero-Pérez, Sonia, Camacho-García, Jorge, Montoro-García, Carlos, López-Pérez, Ana M., Sanz, Alfredo, Mayoral, María José, González-Rodríguez, David
Format: Article
Language:English
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Summary:The preparation and self-assembly of novel G–C dinucleoside monomers that are equipped with electron-poor aryl groups at the G-N 2 amino group have been studied. Such monomers associate via Watson–Crick H-bonding into discrete unstrained tetrameric macrocycles that arise as a thermodynamically and kinetically stabilized product in a wide variety of experimental conditions, including very polar solvent environments and low concentrations. G-arylation produces an increased stability of the cyclic assembly, as a result of a subtle interplay between enthalpic and entropic effects involving the solvent coordination sphere.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01042