Molecular recognition of barbiturates by a metalloreceptor

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

doi:10.1002/recl.19921111002

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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Abstract

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 language	English
Pages (from-to)	421-426
Number of pages	6
Journal	Recueil des travaux chimiques des Pays-Bas
Volume	111
Issue number	10
DOIs	https://doi.org/10.1002/recl.19921111002
Publication status	Published - 1992

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@article{49a1c166ac764364b04839a0098d458b,

title = "Molecular recognition of barbiturates by a metalloreceptor",

abstract = "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.",

author = "{van Doorn}, {Arie R.} and Rushton, {David J.} and {van Straaten-Nijenhuis}, {Wilma F.} and Willem Verboom and Reinhoudt, {David N.}",

year = "1992",

doi = "10.1002/recl.19921111002",

language = "English",

volume = "111",

pages = "421--426",

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

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

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T1 - Molecular recognition of barbiturates by a metalloreceptor

AU - van Doorn, Arie R.

AU - Rushton, David J.

AU - van Straaten-Nijenhuis, Wilma F.

AU - Verboom, Willem

AU - Reinhoudt, David N.

PY - 1992

Y1 - 1992

N2 - 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.

AB - 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.

U2 - 10.1002/recl.19921111002

DO - 10.1002/recl.19921111002

M3 - Article

VL - 111

SP - 421

EP - 426

JO - Recueil des travaux chimiques des Pays-Bas

JF - Recueil des travaux chimiques des Pays-Bas

SN - 0165-0513

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