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Recognition of Helicity by Native Cyclodextrins. Highly Enantioselective Complexation of Tetrahelicene Dicarboxylic Acid with β-Cyclodextrin
20
Citations
9
References
1998
Year
Bioorganic ChemistryNmr SpectroscopyEngineeringMolecular BiologyOrganic ChemistryChemistryChemical BiologyNative CyclodextrinsBiochemistryHighly Enantioselective ComplexationMolecular ChemistrySupramolecular ChemistryNatural Product SynthesisEnantioselective SynthesisAbstract RecognitionBinding ConstantNatural SciencesCyclodextrin ProductionHydrogen BondMolecular ComplexSynthetic ChemistryTetrahelicene Dicarboxylic Acid
Abstract Recognition of the helicity of 1,12-dimethylbenzo[c]-phenanthrene-5,8-dicarboxylic acid (1) by cyclodextrins (CDxs) has been studied by means of 1H NMR spectroscopy. The binding constant (K) for the (M)-1-β-CDx complex is 18700±1700 dm3 mol−1 which is much larger than that of the (P)-1-β-CDx complex (2200±100 dm3 mol−1). The results sugget the formation of the hydrogen bonds between the CO2− groups of 1 and the OH groups of twisted β-CDx in water.
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