Molecular recognition of barbiturates by a metalloreceptor

Arie R. van Doorn, David J. Rushton, Wilma F. van Straaten-Nijenhuis, Willem Verboom, David N. Reinhoudt

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Metallomacrocycle 2, possessing an immobilized Lewis‐acidic uranyl cation, was synthesized by reaction of aldehyde 9 with 1,2‐cis‐cyclohexanediamine in the presence of Ba2+ as a template cation and subsequent transmetallation with UO22+. Docking experiments with barbituric acid revealed that a ‐(CH2)6– spacer between the salen‐uranyl and 2,6‐diamidopyridine moieties of 2 is optimal. According to 1H NMR titration experiments, the barbituric acid complex of 2 is up to 2.7 kcal · mol−1 more stable than the complexes with five disubstituted derivatives. The flux of barbituric acid through a supported liquid membrane is enhanced 3.7 times by carrier 2 mediated transport.
Original languageEnglish
Pages (from-to)421-426
Number of pages6
JournalRecueil des travaux chimiques des Pays-Bas
Issue number10
Publication statusPublished - 1992


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