Molecular recognition of neutral molecules by rigid binaphthyl metalloclefts: synthesis complexation and calculations

Arie R. van Doorn, David J. Rushton, Willem Verboom, David N. Reinhoudt, Marinus Bos

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The binaphthyl metallocleft 2 in which an electrophilic uranyl cation is immobilized was synthesized by reaction of 1,2‐benzenediamine and aldehyde 5. According to 1H‐NMR spectroscopy, 2 is formed as a mixture of meso and racemic diastereomers (ratio 1:0.85). The complexation of 2 with pyridine, (iso)quinoline, acridine, benzylamine, and 1‐naphthalenemethanamine was investigated. The association constants of the complexes with aromatic amines vary from 3.5 · 102 to 3.6 · 106 M−1 (meso‐2) and 1.5 · 102 to 1.0 · 106 M−1 (racemic‐2). The higher stability of the complexes with meso‐2 is in agreement with the results of molecular mechanics calculations.
Original languageEnglish
Pages (from-to)415-420
Number of pages6
JournalRecueil des travaux chimiques des Pays-Bas
Issue number10
Publication statusPublished - 1992


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