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Experimental and computational studies of the binding properties of lower rim tetra- and di-substituted calix[4]arene amide derivatives with metal ions

2016-02-06Journal article Restricted access
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dc.contributor.authorMarcos, Paula M.
dc.contributor.authorFonseca, Joel D.
dc.contributor.authorProença, Carla S.
dc.contributor.authorAscenso, José R.
dc.contributor.authorBernardino, Raul
dc.contributor.authorKulesza, Joanna
dc.contributor.authorBochenska, Maria
dc.date.accessioned2025-06-03T10:01:20Z
dc.date.available2025-06-03T10:01:20Z
dc.date.issued2016-02-06
dc.description.abstractExperimental and theoretical binding studies of representative alkali, alkaline earth, transition, heavy metal and lanthanide cations by tetra- and di-substituted calix[4]arene amide derivatives (diethyl amide 1a–c and morpholide amide 2a–c) in the cone conformation were carried out. Binding was assessed by extraction experiments of the metal picrates from water to dichloromethane and proton NMR titrations. Density functional theory calculations were also performed to determine the binding energy of the complexes formed and to analyse the host–guest interaction modes. In the cases of ligands 1b and 2c with Na+ and Ag+ picrates, the extraction energy was also determined using the polarisable continuum model. The results are discussed in terms of the nature of the amide residue and the substitution pattern (1,3 vs. 1,2). Both tetra-amide derivatives are good extractants, showing preference for Na+, Ca2+, Ag+ and Pb2+ cations, mainly di-ethylamide 1a. Concerning di-amide derivatives, the relative position of the substituents seems to be more important than the nature of the amide group in the extraction process. Proton NMR studies indicate the formation of 1:1 complexes between the amides and the cations studied, and DFT data show that all ligands form the most stable complexes with La3+.eng
dc.identifier.citationMarcos, P. M., Fonseca, J. D., Proença, C. S., Ascenso, J. R., Bernardino, R. J., Kulesza, J., & Bochenska, M. (2016). Experimental and computational studies of the binding properties of lower rim tetra- and di-substituted calix[4]arene amide derivatives with metal ions. Supramolecular Chemistry, 28(5–6), 367–376. https://doi.org/10.1080/10610278.2015.1093631
dc.identifier.doi10.1080/10610278.2015.1093631
dc.identifier.issn1061-0278
dc.identifier.issn1029-0478
dc.identifier.urihttp://hdl.handle.net/10400.8/13072
dc.language.isoeng
dc.peerreviewedyes
dc.publisherInforma UK Limited
dc.relation.hasversionhttps://www.tandfonline.com/doi/full/10.1080/10610278.2015.1093631
dc.relation.ispartofSupramolecular Chemistry
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectCalix[4]arene
dc.subjectTetra- and di-amide derivatives
dc.subjectMetal cation binding
dc.subjectProton NMR titration
dc.subjectDFT
dc.titleExperimental and computational studies of the binding properties of lower rim tetra- and di-substituted calix[4]arene amide derivatives with metal ions
dc.typejournal article
dcterms.referenceshttp://dx.doi.org/10.1080/10610278.2015.1093631
dspace.entity.typePublication
oaire.citation.endPage376
oaire.citation.issue5-6
oaire.citation.startPage367
oaire.citation.titleSupramolecular Chemistry
oaire.citation.volume28
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameBernardino
person.givenNameRaul
person.identifier.orcid0000-0002-7775-0614
person.identifier.ridA-2338-2010
relation.isAuthorOfPublication915a2334-757a-4011-968c-94e7d391b7ac
relation.isAuthorOfPublication.latestForDiscovery915a2334-757a-4011-968c-94e7d391b7ac

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