Molecular recognition of thymine and uracil in water by an amino-, amido-, and carboxymethyl-functionalized pyridinophane

Felipe Medrano, David Octavio Corona-Martínez, Herbert Höpfl, Carolina Godoy-Alcántar*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A new water soluble 26-membered macrocyclic pyridinophane functionalized by amide and carboxymethyl groups has been synthesized in a single step reaction and characterized by elemental analysis, mass spectrometry (FAB+), UV-vis, fluorescence, and 1H NMR spectroscopy as well as single-crystal X-ray diffraction analysis. Its complexation properties with the nucleobases thymine and uracil have been explored in aqueous media by performing 1H NMR titration experiments and potentiometric studies. The binding constants of the 1:1 host-guest complexes were determined as 103M-1 by proton NMR and 102-103M-1 by potentiometry. Semiempirical molecular modelling studies have shown that the nucleobases are included within the cavity of the macrocyclic receptor and that the complexes are stabilized by hydrogen bonding.

Original languageEnglish
Pages (from-to)621-628
Number of pages8
JournalSupramolecular Chemistry
Volume19
Issue number8
DOIs
StatePublished - 1 Dec 2007

Keywords

  • Binding constant
  • Cyclophanes
  • Host-guest complex
  • Molecular recognition
  • NMR
  • Thymine
  • Uracil

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