TY - JOUR
T1 - Molecular recognition of thymine and uracil in water by an amino-, amido-, and carboxymethyl-functionalized pyridinophane
AU - Medrano, Felipe
AU - Corona-Martínez, David Octavio
AU - Höpfl, Herbert
AU - Godoy-Alcántar, Carolina
PY - 2007/12/1
Y1 - 2007/12/1
N2 - 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.
AB - 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.
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U2 - 10.1080/10610270701271850
DO - 10.1080/10610270701271850
M3 - Article
SN - 1061-0278
SP - 621
EP - 628
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
ER -