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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...
A hydrogen‐bonded cyclic tetramer is assembled with remarkably high effective molarities from a properly designed dinucleoside monomer. This self‐assembled species exhibits an impressive thermodynamic and kinetic stability and is formed with high fidelities within a broad concentration range.
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