Synthesis of tris-(azacrown) ethers for carboxylic acid recognition

Michael Lee; Hassan Zali-Boeini; Feng Li; Leonard F. Lindoy; Katrina A. Jolliffe

doi:10.1016/j.tet.2012.10.067

Synthesis of tris-(azacrown) ethers for carboxylic acid recognition

Michael Lee, Hassan Zali-Boeini, Feng Li, Leonard F. Lindoy, Katrina A. Jolliffe

School of Science

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers were synthesised in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by 1H NMR in methanol-d4. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect.

Original language	English
Pages (from-to)	38-42
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2012.10.067
Publication status	Published - 2013

Keywords

carboxylic acids
crown ethers
metal ions

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10.1016/j.tet.2012.10.067

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abstract = "The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers were synthesised in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by 1H NMR in methanol-d4. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect.",

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T1 - Synthesis of tris-(azacrown) ethers for carboxylic acid recognition

AU - Lee, Michael

AU - Zali-Boeini, Hassan

AU - Li, Feng

AU - Lindoy, Leonard F.

AU - Jolliffe, Katrina A.

PY - 2013

Y1 - 2013

N2 - The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers were synthesised in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by 1H NMR in methanol-d4. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect.

AB - The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers were synthesised in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by 1H NMR in methanol-d4. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect.

KW - carboxylic acids

KW - crown ethers

KW - metal ions

UR - http://handle.uws.edu.au:8081/1959.7/524706

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DO - 10.1016/j.tet.2012.10.067

M3 - Article

SN - 1464-5416

VL - 69

SP - 38

EP - 42

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Synthesis of tris-(azacrown) ethers for carboxylic acid recognition

Abstract

Keywords

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