Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Reeske, Gregor; Bradtmöller, Gerrit; Schürmann, Markus; Jurkschat, Klaus

doi:10.1002/chem.200701141

Cited by 46 publications

(37 citation statements)

References 37 publications

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“…It was also shown via 1 H NMR spectroscopic analysis that receptors 22a,b , as well as 21 , are able to extract certain solid sodium halide salts into chloroform solution with several potassium halide salts being partially solubilized (Table 2). Such findings are in agreement with the higher affinity displayed by the calix[4]arene tetra(ethyl ester) derivatives towards the Na + cation than the K + cation 36. The binding mechanism proposed in the case of NaCl and NaBr is conceptually similar to the allosteric action of enzymes and biological receptors, wherein the binding of one ion induces a major conformational change in the receptor such that the affinity to the counter-ion is significantly improved.…”

Section: Ion Pair Receptors Based On Urea Groups For Anion Recognisupporting

confidence: 82%

Ion pair receptors

2010

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Compared with simple ion receptors, which are able to bind either a cation or an anion, ion pair receptors bearing both a cation and an anion recognition site offer the promise of binding ion pairs or pairs of ions strongly as the result of direct or indirect cooperative interactions between co-bound ions. This critical review focuses on the recent progress in the design of ion pair receptors and summarizes the various binding modes that have been used to accommodate ion pairs (110 references).

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Section: Ion Pair Receptors Based On Urea Groups For Anion Recognisupporting

confidence: 82%

Ion pair receptors

2010

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“…This proposed molecular motion serves to break the hydrogen bonds between the urea groups. 36 The binding mechanism proposed in the case of NaCl and NaBr is conceptually similar to the allosteric action of enzymes and biological receptors, wherein the binding of one ion induces a major conformational change in the receptor such that the affinity to the counter-ion is significantly improved. .…”

Section: Ion Pair Receptors Based On Urea Groups For Anion Recognitionmentioning

confidence: 99%

Calix[4]pyrrole-Based Ion Pair Receptors

2014

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Ion pair receptors, which are able to bind concurrently both a cation and an anion, often display higher selectivity and affinity for specific ion pairs than simple ion receptors capable of recognizing primarily either a cation or an anion. This enhancement in recognition function is attributable to direct or indirect cooperative interactions between cobound ions via electrostatic attractions between oppositely charged ions, as well as to positive allosteric effects. In addition, by virtue of binding the counterions of the targeted ion, ion pair receptors can minimize the solvation of the counterions, which can otherwise have a negative effect on the interactions between the receptors and the targeted ions. As a result of their more favorable interactions, ion pair receptors are attractive for use in applications, such as extraction and sensing, where control of the binding interactions is advantageous. In this Account, we illustrate this potential in the context of ion pair receptors based on the calix[4]pyrrole scaffold. Both simple ditopic ion pair receptors, containing sites for the recognition of a single anion and single cation, and so-called multitopic ion pair receptors will be discussed. The latter systems differ from conventional, so-called ditopic ion pair receptors in that they contain more than one binding site for a given targeted ion (e.g., a cation). This permits a level of selectivity and control over binding function not normally seen for simple ion or ion pair receptors containing one or two binding sites, respectively. Calix[4]pyrroles are macrocyclic compounds consisting of four pyrrole units linked via fully substituted sp 3 hybridized meso carbon atoms. They are effective receptors for Lewis basic anions (e.g., halides) in typical organic media and under certain conditions will recognize ion pairs containing charge diffuse cations, such as a small alkylammonium, imidazolium, or cesium cations. The calix[4]pyrrole framework is further attractive in that it is relatively easy to modify. In particular, functionalization of the β-pyrrolic carbon and meso-carbon atoms with simple crown ethers or calix[4]arene crown ethers can produce heteromultitopic ion pair receptors containing more than two cation binding sites. This allows the interactions between receptors and ions to be manipulated on a higher level than can be achieved using simple ion receptors or heteroditopic ion pair receptors and has made these systems attractive for use in ion transport, recognition, and extraction. Recent progress in developing calix[4]pyrroles as both multitopic and more conventional ion pair receptors is summarized in this Account. The emphasis will be on our own work.

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“…Solubilisation of hydrophilic inorganic salts such as alkali metal halides showing high lattice energy into an organic solvent is rather challenging and a topic of general interest . In this context, the synthesis of ditopic receptors capable of simultaneous complexation of both cations and anions is attracting a lot of attention from supramolecular chemists . Ditopic receptors overcome the shortcomings of ion‐pairing effects involved in the recognition processes of simple anion or cation receptors, and therefore have the ability to dissolve hydrophilic inorganic species.…”

Section: Introductionmentioning

confidence: 99%

Organotin‐Functionalized Crown Ethers as Ditopic Hosts for Lithium Salts: Synthesis, Structures and Complexation Studies of X₃SnCH₂[16]‐crown‐5 (X = I, Br, Cl)

et al. 2018

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The syntheses of the organotin-substituted crown ethers X 3 SnCH 2 [16]-crown-5 (2, X = I; 3, X = Br; 4, X = Cl), and the organostannate complex Ph 4 P[4·Cl] are reported. These compounds are characterized by 1 H, 13 C, and 119 Sn, NMR spectroscopy, elemental analyses, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction studies. The solidstate structure of 2 is characterized by two intramolecular O→Sn interactions, whereas 3 and 4 each contain one intraand one intermolecular O→Sn interactions involving crown ether and water oxygen atoms. The tin atoms are six-coordinate [a] Figure 4. Representative 1 H NMR spectra in CD 3 CN solution of 3 (bottom), 3 after addition of four molar equivalents of NaBr (centre) and of 3 after addition of four molar equivalents of LiBr (top).Eur. J. Inorg. Chem. 2018, 1540-1545 www.eurjic.org

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Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Cited by 46 publications

References 37 publications

Ion pair receptors

Ion pair receptors

Calix[4]pyrrole-Based Ion Pair Receptors

Organotin‐Functionalized Crown Ethers as Ditopic Hosts for Lithium Salts: Synthesis, Structures and Complexation Studies of X₃SnCH₂[16]‐crown‐5 (X = I, Br, Cl)

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Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Cited by 46 publications

References 37 publications

Ion pair receptors

Ion pair receptors

Calix[4]pyrrole-Based Ion Pair Receptors

Organotin‐Functionalized Crown Ethers as Ditopic Hosts for Lithium Salts: Synthesis, Structures and Complexation Studies of X3SnCH2[16]‐crown‐5 (X = I, Br, Cl)

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Organotin‐Functionalized Crown Ethers as Ditopic Hosts for Lithium Salts: Synthesis, Structures and Complexation Studies of X₃SnCH₂[16]‐crown‐5 (X = I, Br, Cl)