Molecular recognition of carbonyl compounds by uranyl-salophen based neutral receptors driven by Van der Waals forces

V. van Axel castelli, Valeria van Axel Castelli, Antonella Dalla Cort, Luigi Mandolini, Valentina Pinto, David Reinhoudt, Fabrizio Ribaudo, Cecilia Sanna, Luca Schiaffino, Bianca H.M. Ruel

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    31 Citations (Scopus)

    Abstract

    The complexation of the salophen-uranyl metallocleft 2 and of its half-cleft analogue 3 with enones and other carbonyl compounds was assessed in chloroform by UV-Vis titration and, occasionally, by FT-IR measurements. Complexes with receptors 2 and 3 are in all cases more stable than those with the control unsubstituted uranyl-salophen 1 , showing that in addition to the primary binding force provided by coordination of the carbonyl oxygen to the uranium, a significant driving force for complexation, typically in the range of 2-3 kcal/mol, results from van der Waals interactions of the guest with the aromatic walls. Replacement of the phenyl group in 3 with larger aromatic residues to give 4 and 5 , led to enhanced complex stabilities, due to more extended contact surfaces between host and guest.
    Original languageUndefined
    Pages (from-to)211-219
    JournalSupramolecular chemistry
    Volume14
    Issue number2-3
    DOIs
    Publication statusPublished - 2002

    Keywords

    • van der Waals forces
    • Neutral molecule recognition
    • Enone guests
    • IR-37947
    • Ketone guests
    • METIS-206206
    • Uranyl-salophen

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