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Bell SE, Browne JK, McKee V, et al. Cation Complexation by Chemically Modified Calixarenes. 11. Complexation and Extraction of Alkali Cations by Calix[5]- and -[6]arene Ketones. Crystal and Molecular Structures of Calix[5]arene Ketones and Na(+) and Rb(+) Complexes. J Org Chem. 1998;63(3):489-501doi: 10.1021/jo9713114.
Bell, S. E., Browne, J. K., McKee, V., McKervey, M. A., Malone, J. F., O'Leary, M., Walker, A., Arnaud-Neu, F., Boulangeot, O., Mauprivez, O., & Schwing-Weill, M. J. (1998). Cation Complexation by Chemically Modified Calixarenes. 11. Complexation and Extraction of Alkali Cations by Calix[5]- and -[6]arene Ketones. Crystal and Molecular Structures of Calix[5]arene Ketones and Na(+) and Rb(+) Complexes. The Journal of organic chemistry, 63(3), 489-501. https://doi.org/10.1021/jo9713114
Bell, Steven E. J., et al. "Cation Complexation by Chemically Modified Calixarenes. 11. Complexation and Extraction of Alkali Cations by Calix[5]- and -[6]arene Ketones. Crystal and Molecular Structures of Calix[5]arene Ketones and Na(+) and Rb(+) Complexes." The Journal of organic chemistry vol. 63,3 (1998): 489-501. doi: https://doi.org/10.1021/jo9713114
Bell SE, Browne JK, McKee V, McKervey MA, Malone JF, O'Leary M, Walker A, Arnaud-Neu F, Boulangeot O, Mauprivez O, Schwing-Weill MJ. Cation Complexation by Chemically Modified Calixarenes. 11. Complexation and Extraction of Alkali Cations by Calix[5]- and -[6]arene Ketones. Crystal and Molecular Structures of Calix[5]arene Ketones and Na(+) and Rb(+) Complexes. J Org Chem. 1998 Feb 06;63(3):489-501. doi: 10.1021/jo9713114. PMID: 11672037.
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J Org Chem. 1998 Feb 06;63(3):489-501. doi: 10.1021/jo9713114.

Cation Complexation by Chemically Modified Calixarenes. 11. Complexation and Extraction of Alkali Cations by Calix[5]- and -[6]arene Ketones. Crystal and Molecular Structures of Calix[5]arene Ketones and Na(+) and Rb(+) Complexes.

The Journal of organic chemistry

Steven E. J. Bell, Julie K. Browne, Vickie McKee, M. Anthony McKervey, John F. Malone, Maeve O'Leary, Andrew Walker, Francoise Arnaud-Neu, Olivier Boulangeot, Olivier Mauprivez, Marie-Jose Schwing-Weill

Affiliations

  1. Laboratoire de Chimie-Physique, URA au CNRS 405, ECPM, 1, rue Blaise Pascal, 67000 Strasbourg, France.

PMID: 11672037 DOI: 10.1021/jo9713114

Abstract

A series of four calix[5]arenes and three calix[6]arenes (R-calixarene-OCH(2)COR(1)) (R = H or Bu(t)) with alkyl ketone residues (R(1) = Me or Bu(t)) on the lower rim have been synthesized, and their affinity for complexation of alkali cations has been assessed through phase-transfer experiments and stability constant measurements. The conformations of these ketones have been probed by (1)H NMR and X-ray diffraction analysis, and by molecular mechanics calculations. Pentamer 3 (R = R(1) = Bu(t)) possesses a symmetrical cone conformation in solution and a very distorted cone conformation in the solid state. Pentamer 5 (R = H, R(1) = Bu(t)) exists in a distorted 1,2-alternate conformation in the solid state, but in solution two slowly interconverting conformations, one a cone and the other presumed to be 1,2-alternate, can be detected. X-ray structure analysis of the sodium and rubidium perchlorate complexes of 3 reveal the cations deeply encapsulated by the ethereal and carbonyl oxygen atoms in distorted cone conformations which can be accurately reproduced by molecular mechanics calculations. The phase-transfer and stability constant data reveal that the extent of complexation depends on calixarene size and the nature of the alkyl residues adjacent to the ketonic carbonyls with tert-butyl much more efficacious than methyl.

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