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Alkali and alkaline-earth metal cation complexation and transport properties by tetraphenyl ketone ofp-tert-butyldihomooxacalix[4]arene

1999; Wiley; Volume: 12; Issue: 9 Linguagem: Inglês

10.1002/(sici)1099-1395(199909)12

1099-1395

Paula M. Marcos, José R. Ascenso, Manuel A. P. Segurado, J. L. C. Pereira,

Crystallography and molecular interactions

Journal of Physical Organic ChemistryVolume 12, Issue 9 p. 695-702 Research Article Alkali and alkaline-earth metal cation complexation and transport properties by tetraphenyl ketone of p-tert-butyldihomooxacalix[4]arene Paula M. Marcos, Corresponding Author Paula M. Marcos Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CiTecMat, Rua da Escola Politécnica 58, 1250-102 Lisboa, Portugal Faculdade de Farmácia da Universidade de Lisboa, Av. das Forças Armadas, 1600 Lisboa, PortugalFaculdade de Ciências da Universidade de Lisboa, Departmento de Química/CiTecMat, Rua da Escola Politécnica 58, 1250-102 Lisboa, Portugal===Search for more papers by this authorJosé R. Ascenso, José R. Ascenso Instituto Superior Técnico, Complexo I, Av. Rovisco Pais, 1096 Lisboa Codex, PortugalSearch for more papers by this authorManuel A. P. Segurado, Manuel A. P. Segurado Faculdade de Farmácia da Universidade de Lisboa, Av. das Forças Armadas, 1600 Lisboa, PortugalSearch for more papers by this authorJ. L. C. Pereira, J. L. C. Pereira Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CiTecMat, Rua da Escola Politécnica 58, 1250-102 Lisboa, PortugalSearch for more papers by this author Paula M. Marcos, Corresponding Author Paula M. Marcos Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CiTecMat, Rua da Escola Politécnica 58, 1250-102 Lisboa, Portugal Faculdade de Farmácia da Universidade de Lisboa, Av. das Forças Armadas, 1600 Lisboa, PortugalFaculdade de Ciências da Universidade de Lisboa, Departmento de Química/CiTecMat, Rua da Escola Politécnica 58, 1250-102 Lisboa, Portugal===Search for more papers by this authorJosé R. Ascenso, José R. Ascenso Instituto Superior Técnico, Complexo I, Av. Rovisco Pais, 1096 Lisboa Codex, PortugalSearch for more papers by this authorManuel A. P. Segurado, Manuel A. P. Segurado Faculdade de Farmácia da Universidade de Lisboa, Av. das Forças Armadas, 1600 Lisboa, PortugalSearch for more papers by this authorJ. L. C. Pereira, J. L. C. Pereira Faculdade de Ciências da Universidade de Lisboa, Departamento de Química/CiTecMat, Rua da Escola Politécnica 58, 1250-102 Lisboa, PortugalSearch for more papers by this author First published: 14 September 1999 https://doi.org/10.1002/(SICI)1099-1395(199909)12:9 3.0.CO;2-TCitations: 23AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The tetraphenyl ketone of p-tert-butyldihomooxacalix[4]arene (2) was synthesized for the first time. This derivative possesses the cone conformation in solution at room temperature, which was confirmed by NMR measurements (1H, 13C and NOE 1D). Extraction studies with metal picrates from neutral aqueous solution into dichloromethane, transport experiments with metal picrates through a dichloromethane membrane and stability constant measurements by UV absorption spectroscopy in methanol and acetonitrile were performed to evaluate the binding ability of ketone 2 towards alkali and alkaline earth metal cations. The tetraphenylketone of p-tert-butylcalix[4]arene (3) was also studied, and the results for the two derivatives were compared. Compound 2 shows a preference for K+ and Ba2+ cations, being selective only in the alkaline earth metal cation series. 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