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

✍ Scribed by Arie R. van Doorn; David J. Rushton; Willem Verboom; David N. Reinhoudt; Marinus Bos

• Book ID: 104589452
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 611 KB
• Volume: 111
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19921111001

✦ Synopsis

Abstract

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 ^1^H‐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 · 10^2^ to 3.6 · 10^6^ M^−1^ (meso‐2) and 1.5 · 10^2^ to 1.0 · 10^6^ M^−1^ (racemic‐2). The higher stability of the complexes with meso‐2 is in agreement with the results of molecular mechanics calculations.