Preorganized endo-dicarboxylic host macrocycles having superior extraction selectivity for small alkaline earth metal ions

Gloe, Karsten; Stephan, Holger; Heitzsch, Olaf; Bukowsky, Heinz; Uhlemann, E.; Pollex, Rolf; Weber, Edwin

doi:10.1039/c39940001955

Cited by 7 publications

(3 citation statements)

References 5 publications

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“…4. The data obtained with slopes of unity were consistent with preferential 1 : 1 complex formation 20 for Ca 2+ , Sr 2+ , Ba 2+ and Na + , as had been surmised from the NMR titration data in CD 3 OD.…”

Section: Liquid-liquid Extraction Behaviour Of Ligands 9 and 1bsupporting

confidence: 85%

“…Given that the ionophore in membrane-based ion-selective electrodes serves to transport selectively the target ion from an aqueous phase into a relatively fluid, plasticised PVC matrix, relevant and useful information about the efficacy of ionophores may be obtained by examining the phase transfer of various metal ions from aqueous to different lipophilic organic phases. 20 With ligand 9, and also 1b, liquid-liquid extraction investigations were performed in micro-reaction vials in buffered aqueous media (298 K, pH 5.2) and toluene or chloroform. The hexadentate ligand 9 showed some evidence for Na + / K + selectivity in extraction (Fig.…”

Section: Liquid-liquid Extraction Behaviour Of Ligands 9 and 1bmentioning

confidence: 99%

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Selective cation binding with cis,cis-1,3,5-trioxycyclohexyl based ligands: application to ion transport and electrochemical detection and assessment of complexation by electrospray mass spectrometry

Goodall¹,

Kelly²,

Parker³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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Section: Liquid-liquid Extraction Behaviour Of Ligands 9 and 1bsupporting

confidence: 85%

Section: Liquid-liquid Extraction Behaviour Of Ligands 9 and 1bmentioning

confidence: 99%

Selective cation binding with cis,cis-1,3,5-trioxycyclohexyl based ligands: application to ion transport and electrochemical detection and assessment of complexation by electrospray mass spectrometry

Goodall¹,

Kelly²,

Parker³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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“…9 Recently we reported a macrocyclic structure based on this design featuring two convergent carboxylic acid functions kept at a non-interactive distance. 10 These preorganised macrocycles were found to extract small alkaline earth metal ions in a liquid two-phase system with high selectivity. They also make possible selective inclusion of organic molecules.…”

Section: Introductionmentioning

confidence: 99%

Structure and kinetics of novel cyclophane inclusion compounds

Apel¹,

Czugler²,

Griffith³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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A novel cyclophane host compound, 3, featuring a macrocyclic structure with two hydroquinone dimethyl ether and two 1,1-diphenylcyclohexane construction elements assembled via benzylic ether linkages has been synthesised and its inclusion compounds with toluene, 4, and cyclohexanone, 5, have been characterised by thermal analysis and X-ray crystallography. The conformation of the cyclophane is markedly different in the two inclusion compounds. The kinetics of desolvation of 5 are deceleratory and yield an activation energy of 182 kJ mol Ϫ1 .

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Molecular Recognition

Weber¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Molecular recognition is a central point. It may be said that without molecular recognition, there would be no life on this world. Vital biochemical processes such as enzyme action, molecular transport, genetic information, processing and protein assembly all involve molecular recognition as an essential action. Understanding of its principles is still a problem although a first elucidation of the rules that govern molecular recognition dates back to the late nineteenth century. The “lock‐and‐key” principle (1894) proposed that enzyme and substrate can be compared to lock and key getting selectivity between molecules involved. Earlier it was recognized that molecules do not act if they do not bind, thus introducing the concept of receptor. Finally binding or fixation requires interaction, affinity between the partners, that may be related to the idea of coordination of Werner. According to these basic concepts, molecular recognition implies complementary lock‐and‐key type fit between molecules. The lock is the molecular receptor and the key being the substrate that is recognized and selected to give a defined receptor–substrate complex, a coordination compound or a supermolecule. Hence molecular recognition is one of the three main pillars, fixation, coordination, and recognition, that lay foundation of what is now called supramolecular chemistry.

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Preorganized endo-dicarboxylic host macrocycles having superior extraction selectivity for small alkaline earth metal ions

Abstract: Novel preorganized host macrocycles with defined cavity size and t w o convergent carboxylic acid groups extract small alkaline earth metal ions in a liquid two-phase system with high selectivity, in particular Ca2+, unlike the alkali metal ions.

Cited by 7 publications

References 5 publications

Selective cation binding with cis,cis-1,3,5-trioxycyclohexyl based ligands: application to ion transport and electrochemical detection and assessment of complexation by electrospray mass spectrometry

Selective cation binding with cis,cis-1,3,5-trioxycyclohexyl based ligands: application to ion transport and electrochemical detection and assessment of complexation by electrospray mass spectrometry

Structure and kinetics of novel cyclophane inclusion compounds

Molecular Recognition

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