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Oligoamide Foldamers as Helical Chloride Receptors-the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions.
Helttunen, Kaisa; Annala, Riia; Suhonen, Aku; Iloniemi, Juho; Kalenius, Elina; Aragay, Gemma; Ballester, Pablo; Tuononen, Heikki M; Nissinen, Maija.
Afiliação
  • Helttunen K; Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014, Jyvaskyla, Finland.
  • Annala R; Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014, Jyvaskyla, Finland.
  • Suhonen A; Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014, Jyvaskyla, Finland.
  • Iloniemi J; Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014, Jyvaskyla, Finland.
  • Kalenius E; Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014, Jyvaskyla, Finland.
  • Aragay G; Institute of Chemical Research of Catalonia (ICIQ), Avgda., Països Catalans 16, 43007, Tarragona, Spain.
  • Ballester P; Institute of Chemical Research of Catalonia (ICIQ), Avgda., Països Catalans 16, 43007, Tarragona, Spain.
  • Tuononen HM; Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluís Companys 23, 08010, Barcelona, Spain.
  • Nissinen M; Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box 35, 40014, Jyvaskyla, Finland.
Chem Asian J ; 14(5): 647-654, 2019 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-30644629
ABSTRACT
The anion-binding properties of three closely related oligoamide foldamers were studied using NMR spectroscopy, isothermal titration calorimetry and mass spectrometry, as well as DFT calculations. The 1 H NMR spectra of the foldamers in [D6 ]acetone solution revealed partial preorganization by intramolecular hydrogen bonding, which creates a suitable cavity for anion binding. The limited size of the cavity, however, enabled efficient binding by the inner amide protons only for the chloride anion resulting in the formation of a thermodynamically stable 11 complex. All 11 chloride complexes displayed a significant favourable contribution of the entropy term. Most likely, this is due to the release of ordered solvent molecules solvating the free foldamer and the anion to the bulk solution upon complex formation. The introduction of electron-withdrawing substituents in foldamers 2 and 3 had only a slight effect on the thermodynamic constants for chloride binding compared to the parent receptor. Remarkably, the binding of chloride to foldamer 3 not only produced the expected 11 complex but also open aggregates with 12 (hostanion) stoichiometry.

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Texto completo: Disponível Coleções: Bases de dados internacionais Base de dados: MEDLINE Idioma: Inglês Revista: Chem Asian J Ano de publicação: 2019 Tipo de documento: Artigo País de afiliação: Finlândia