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

doi:10.1002/recl.19921111001

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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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 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 language	English
Pages (from-to)	415-420
Number of pages	6
Journal	Recueil des travaux chimiques des Pays-Bas
Volume	111
Issue number	10
DOIs	https://doi.org/10.1002/recl.19921111001
Publication status	Published - 1992

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@article{841e1c3e1745454aaa45a9f27b4a4367,

title = "Molecular recognition of neutral molecules by rigid binaphthyl metalloclefts: synthesis complexation and calculations",

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 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.",

author = "{van Doorn}, {Arie R.} and Rushton, {David J.} and Willem Verboom and Reinhoudt, {David N.} and Marinus Bos",

year = "1992",

doi = "10.1002/recl.19921111001",

language = "English",

volume = "111",

pages = "415--420",

journal = "Recueil des travaux chimiques des Pays-Bas",

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

number = "10",

}

TY - JOUR

T1 - Molecular recognition of neutral molecules by rigid binaphthyl metalloclefts

T2 - synthesis complexation and calculations

AU - van Doorn, Arie R.

AU - Rushton, David J.

AU - Verboom, Willem

AU - Reinhoudt, David N.

AU - Bos, Marinus

PY - 1992

Y1 - 1992

N2 - 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.

AB - 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.

U2 - 10.1002/recl.19921111001

DO - 10.1002/recl.19921111001

M3 - Article

VL - 111

SP - 415

EP - 420

JO - Recueil des travaux chimiques des Pays-Bas

JF - Recueil des travaux chimiques des Pays-Bas

SN - 0165-0513

IS - 10

ER -