Utilize este identificador para referenciar este registo: http://hdl.handle.net/10451/20909
Título: 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
Autor: Marcos, Paula M.
Ascenso, Jose R.
Segurado, Manuel A. P.
Bernardino, Raul J.
Cragg, Peter J.
Palavras-chave: Chemistry, Organic
Data: 2009
Citação: TETRAHEDRON. - Vol. 65, n. 2 (2009), p. 496-503
Resumo: 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 (H-1 and C-13). 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. (C) 2008 Elsevier Ltd. All rights reserved.
URI: http://hdl.handle.net/10451/20909
DOI: http://dx.doi.org/10.1016/j.tet.2008.11.005
ISSN: 0040-4020
Aparece nas colecções:FF - Produção Científica 2000-2009

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