1994
DOI: 10.1039/dt9940003637
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Design and synthesis of ionophores with multiple receptor sites: solution nuclear magnetic resonance studies of their interaction with chloride, sodium and potassium ions

Abstract: lonophores of the bis(crown ether) type, with polyamine linkers, examples of which are known to bind simultaneously to a cation and its counter anion, have been prepared. One-pot reductive amination, used to couple a benzo-crown aldehyde with aliphatic (both linear and cyclic) and aromatic polyamines, proved to be the most efficient route. A strong inhibition of one synthetic route (amine benzylation) was observed.The competitive interaction between chloride and other anions for binding with the protonated ion… Show more

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Cited by 18 publications
(24 citation statements)
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“…The residue was stirred in diethyl ether and the solvent removed under vacuum to give the product as a white solid (0.91 g, 94% yield). 1 H NMR (300 MHz, CDCl 3 ): δ 1.32 (m, 9H, OCH 2 CH 3 ), 3.32 (d (J = 13), 2H, CCH 2 C), 3.35 (d (J = 13), 4H, CCH 2 C) and 6.48-7.14 (m, 12H, ArH) Microanalysis: C 42 H 44 O 12 ؒ0.5H 2 O requires C 67.28, H 6.05%; found C 67.39, H 5.93%, [4]arene 3. Compound 2 (1.00 g, 1.35 mmol) was refluxed in oxalyl chloride for 2 hours.…”
Section: Solvent and Reagent Pretreatmentmentioning
confidence: 99%
See 1 more Smart Citation
“…The residue was stirred in diethyl ether and the solvent removed under vacuum to give the product as a white solid (0.91 g, 94% yield). 1 H NMR (300 MHz, CDCl 3 ): δ 1.32 (m, 9H, OCH 2 CH 3 ), 3.32 (d (J = 13), 2H, CCH 2 C), 3.35 (d (J = 13), 4H, CCH 2 C) and 6.48-7.14 (m, 12H, ArH) Microanalysis: C 42 H 44 O 12 ؒ0.5H 2 O requires C 67.28, H 6.05%; found C 67.39, H 5.93%, [4]arene 3. Compound 2 (1.00 g, 1.35 mmol) was refluxed in oxalyl chloride for 2 hours.…”
Section: Solvent and Reagent Pretreatmentmentioning
confidence: 99%
“…Stimulated by the need to design new selective extraction and transportation reagents for metal salt species of environmental and biological importance, ion pair recognition, the simultaneous binding of cationic and anionic guest species by ditopic receptors, is a rapidly developing new field of coordination chemistry. [1][2][3][4][5][6][7][8][9][10][11][12][13] Novel co-operative and allosteric metal salt complexing behaviour whereby the binding of the metal cation charged guest can enhance, through electrostatic and conformational effects, the subsequent coordination of the pairing anion has been demonstrated by a number of ditopic crown ether functionalised boron, 1 uranyl, 2 polyammonium, 3 amide, 6-12 urea 11 and amide 4, 13 -urea calix [4]arene 5 based receptor systems. In addition such systems have recently been shown to solubilise and transport alkali metal salts across lipophilic membranes.…”
mentioning
confidence: 99%
“…The synthesis of ditopic receptors, which interact simultaneously with cationic and anionic guests in so called ion-pair recognition processes, is a rapidly developing area of research (McConnell & Beer, 2012). A number of ditopic receptors based on a macrocylic or acyclic scaffold have been designed and studied (Kinnear et al (1994), Kirkovits et al (2001), Hossain & Schneider (1998), Tsukube et al (1999) and Smith (2010)) Interesting applications, such as binding of amino acids in their zwitterionic state, salt extraction and membrane transport, have been reported in the literature (for a recent review, see McConnell & Beer, 2012). In this context, the title compound is a particularly useful building block for the construction of a large number of receptors with different recognition units, because it provides a base for many synthetic modifications of the molecule structure.…”
Section: S1 Commentmentioning
confidence: 99%
“…Ion pair recognition, the simultaneous complexation of cationic and anionic guest species by multisite receptors, is a new, emerging and topical field of coordination chemistry. [1][2][3][4][5][6] These heteroditopic ligands can be designed to exhibit novel cooperative and allosteric behaviour whereby the binding of one charged guest can influence, through electrostatic and conformational effects, the subsequent coordination of the pairing ion. Such systems have potential as new selective extraction and transportation reagents for ion pair species of environmental importance.…”
mentioning
confidence: 99%