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Complexation of Ions and Neutral Molecules by Functionalized Calixarenes

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Computational Approaches in Supramolecular Chemistry

Part of the book series: NATO ASI Series ((ASIC,volume 426))

Abstract

The possibility of controlling the stereochemical outcome in the alkylation of calix[4]arenes at the lower rim has allowed a better control of selectivity and efficiency in metal ion recognition by calixarene-based ligands. The combination of polar binding groups (ester and amide) on a polar calixarene structure (cone) produces ionophores which are selective toward cations with high charge density such as sodium and calcium. In calix[4]arene crown ethers the size of the ring and the conformation of the calix determine efficiency and selectivity. In the partial cone and more in the 1,3-alternate conformation, the complexed cation is stabilized by cation/π interactions, which seem to favour cesium over other alkali metal cations. Calix[4]arenes having alkyl groups at the upper rim are able to recognize aromatic guest molecules in the solid state showing selectivity toward benzene and p-xylene. The recognition process seems to be controlled by the nature of the alkyl substituent at the upper rim which make it possible the operation of weak CH/π interactions. The role of such interactions in Supramolecular Chemistry and in other chemical phenomena is briefly reviewed.

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Authors and Affiliations

  1. Dipartimento di Chimica Organica e Industriale, Italy

    R. Ungaro, A. Arduini, A. Casnati & A. Pochini

  2. Istituto di Chimica Generale ed Inorganica dell’Università degli Studi di Parma, Viale delle Scienze, I-43100, Parma, Italy

    O. Ori & F. Ugozzoli

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  1. R. Ungaro
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  2. A. Arduini
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  3. A. Casnati
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  4. O. Ori
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  5. A. Pochini
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  6. F. Ugozzoli
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Editors and Affiliations

  1. Laboratory of Molecular Modeling and Simulations, URA-CNRS, University Louis Pasteur, Strasbourg, France

    Georges Wipff

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Ungaro, R., Arduini, A., Casnati, A., Ori, O., Pochini, A., Ugozzoli, F. (1994). Complexation of Ions and Neutral Molecules by Functionalized Calixarenes. In: Wipff, G. (eds) Computational Approaches in Supramolecular Chemistry. NATO ASI Series, vol 426. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-1058-7_19

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  • DOI: https://doi.org/10.1007/978-94-011-1058-7_19

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