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Synthesis, binding properties and theoretical studies of p-tert-butylhexahomotrioxacalix[3]arene tri(adamantyl)ketone with alkali, alkaline earth, transition, heavy metal and lanthanide cations

2009-01Artigo científico Acesso aberto
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dc.contributor.authorMarcos, Paula M.
dc.contributor.authorAscenso, José R.
dc.contributor.authorSegurado, Manuel A.P.
dc.contributor.authorBernardino, Raul J.
dc.contributor.authorCragg, Peter J.
dc.contributor.authorBernardino, Raul
dc.date.accessioned2025-04-15T11:46:31Z
dc.date.available2025-04-15T11:46:31Z
dc.date.issued2009-01
dc.description.abstractp-tert-Butylhexahomotrioxacalix[3]arene tri(adamantyl)ketone (1b) was synthesized for the first time. Compound 1b was obtained in a cone conformation in solution at room temperature, as established by NMR spectroscopy (1H and 13C). The binding properties of ligand 1b for alkali, alkaline earth, transition, heavy metal and lanthanide cations have been assessed by phase transfer and proton NMR titration experiments. Molecular mechanics and ab initio techniques were also employed to complement the NMR data. The results are compared to those obtained with other closely related homooxacalixarene derivatives. Although triketone 1b is a weak extractant, it shows a strong peak selectivity for Na+ and also some preference for Ag+. Proton NMR titrations indicate the formation of 1:1 complexes between 1b and the cations studied, and also that they should be located inside the cavity defined by the phenoxy and carbonyl oxygen atoms. Although the molecular mechanics results show little correlation with the NMR data, a good agreement was obtained with the ab initio models.eng
dc.identifier.citationPaula M. Marcos, José R. Ascenso, Manuel A.P. Segurado, Raul J. Bernardino, Peter J. Cragg, Synthesis, binding properties and theoretical studies of p-tert-butylhexahomotrioxacalix[3]arene tri(adamantyl)ketone with alkali, alkaline earth, transition, heavy metal and lanthanide cations, Tetrahedron, Volume 65, Issue 2, 2009, Pages 496-503, ISSN 0040-4020, https://doi.org/10.1016/j.tet.2008.11.005.
dc.identifier.doi10.1016/j.tet.2008.11.005
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/10400.8/12798
dc.language.isoeng
dc.peerreviewedyes
dc.publisherElsevier BV
dc.relation.hasversionhttps://www.sciencedirect.com/science/article/pii/S0040402008019479?pes=vor&utm_source=scopus&getft_integrator=scopus
dc.relation.ispartofTetrahedron
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectCalixarenes
dc.subjectHexahomotrioxacalix[3]arene ketone
dc.subjectMetal cation extraction
dc.subjectProton NMR titration
dc.subjectMolecular mechanics
dc.subjectAb initio
dc.titleSynthesis, binding properties and theoretical studies of p-tert-butylhexahomotrioxacalix[3]arene tri(adamantyl)ketone with alkali, alkaline earth, transition, heavy metal and lanthanide cationseng
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage503
oaire.citation.issue2
oaire.citation.startPage496
oaire.citation.titleTetrahedron
oaire.citation.volume65
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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p-tert-Butylhexahomotrioxacalix[3]arene tri(adamantyl)ketone (1b) was synthesized for the first time. Compound 1b was obtained in a cone conformation in solution at room temperature, as established by NMR spectroscopy (1H and 13C). The binding properties of ligand 1b for alkali, alkaline earth, transition, heavy metal and lanthanide cations have been assessed by phase transfer and proton NMR titration experiments. Molecular mechanics and ab initio techniques were also employed to complement the NMR data. The results are compared to those obtained with other closely related homooxacalixarene derivatives. Although triketone 1b is a weak extractant, it shows a strong peak selectivity for Na+ and also some preference for Ag+. Proton NMR titrations indicate the formation of 1:1 complexes between 1b and the cations studied, and also that they should be located inside the cavity defined by the phenoxy and carbonyl oxygen atoms. Although the molecular mechanics results show little correlation with the NMR data, a good agreement was obtained with the ab initio models.
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