Open AccessMolecular recognition of neutral molecules by rigid binaphthyl metalloclefts: Synthesis, complexation and calculations
Author(s) -
van Doorn Arie R.,
Rushton David J.,
Verboom Willem,
Reinhoudt David N.,
Bos Marinus
Publication year - 1992
Publication title -
recueil des travaux chimiques des pays‐bas
Language(s) - English
Resource type - Journals
ISSN - 0165-0513
DOI - 10.1002/recl.19921111001
Subject(s) - chemistry , quinoline , pyridine , acridine , diastereomer , benzylamine , molecule , electrophile , nuclear magnetic resonance spectroscopy , adduct , medicinal chemistry , aldehyde , stereochemistry , organic chemistry , catalysis
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.
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