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The effect of substitution pattern on binding ability in regioisomeric ion pair receptors based on an aminobenzoic platform

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dc.abstract.enA series of ditopic ion pair receptors equipped with 4-nitrophenylurea and 1-aza-18-crown-6-ether linked by ortho-(1), meta-(2), and para-(3) substituted benzoic acid were readily synthesized in three steps from commercially available materials. The binding properties of these regioisomeric receptors were determined using UV-vis and 1H NMR spectroscopy in MeCN and in the solid state by single-crystal X-ray diffraction crystallography. The solution studies revealed that, apart from carboxylates, all the anions tested formed stronger complexes in the presence of sodium cations. Receptors 2 and 3 were found to interact with ion pairs with remarkably higher affinity than ortho-substituted 1. 1H NMR titration experiments showed that both urea NH protons interacted with anions with comparable strength in the case of receptors 2 and 3, but only one of the NHs was effective in anion binding in the case of receptor 1. X-ray analysis of the crystal structure of receptor 1 and 1·NaPF6 complex showed that binding was hampered due to the formation of an intramolecular hydrogen bond. Analysis of the crystal structures of 2·NaBr and 3·NaBr complexes revealed that proper mutual orientation of binding domains was responsible for the improved binding of the sodium salts.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorDąbrowa, Kajetan
dc.contributor.authorZiach, Krzysztof
dc.contributor.authorRomański, Jan
dc.contributor.authorJagleniec, Damian
dc.date.accessioned2024-01-26T10:11:38Z
dc.date.available2024-01-26T10:11:38Z
dc.date.copyright2019-08-18
dc.date.issued2019
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number16
dc.description.versionFINAL_PUBLISHED
dc.description.volume24
dc.identifier.doi10.3390/MOLECULES24162990
dc.identifier.issn1420-3049
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/122208
dc.identifier.weblinkhttps://doi.org/10.3390/molecules24162990
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofMolecules
dc.relation.pages2990
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enIon pair receptors
dc.subject.enMolecular recognition
dc.subject.enNMR spectroscopy
dc.subject.enSalt binding
dc.subject.enSubstitution effects
dc.subject.enUV-Vis spectroscopy
dc.titleThe effect of substitution pattern on binding ability in regioisomeric ion pair receptors based on an aminobenzoic platform
dc.typeJournalArticle
dspace.entity.typePublication