Abstract
From the reaction ofp-t-butylcalix[4]arene with α-chloro-N,N-diethyl acetamide a new lipophilic ether-amide ligand (2) has been obtained in high yield. Solution studies show (2) to be a very strong cation receptor for alkali cations, especially sodium and potassium. The X-ray crystal structure determination of the free ligand (2) and two potassium complexes (KI and KSCN) shows the calix[4]arene in a fixed ‘cone’ structure and the cation completely encapsulated in a polar cavity of eight oxygen atoms.
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References and Notes
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We thank a referee for suggesting that the presence in ligand (2) of ether-amide binding groups could enhance its complexing ability toward alkaline-earth cations, by analogy with calcium-selective ether-amide podands (cf. W. E. Morfet al.: Progress in Macrocyclic Chemistry (R. M. Izatt and J. J. Christensen, Eds.) Wiley-Interscience 1979, p. 1).1H titration experiments, similar to that described in this paper, show that ligand (2) is indeed able to complex Ca(SCN)2 in CDCl3 with a 1∶1 stoichiometry. However, since we do not have the overall picture of the association constants, we cannot discuss the problem of monovalent/divalent cation selectivity of our ligand (2).
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Supplementary Data relating to this article are deposited with the British Library as supplementary publication No. SUP 82059 (57 pages).
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Arduini, A., Ghidini, E., Pochini, A. et al. p-t-Butylcalix[4]arene tetra-acetamide: a new strong receptor for alkali cations [1]. Journal of Inclusion Phenomena 6, 119–134 (1988). https://doi.org/10.1007/BF00663045
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DOI: https://doi.org/10.1007/BF00663045