Encapsulation of tetramethylphosphonium cations

Beyeh, Ngong Kodiah; Valkonen, Arto; Rissanen, Kari

doi:10.1080/10610270802308411

Cited by 26 publications

(14 citation statements)

References 21 publications

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“…[229] Wegen ihrer elektronenreichen Natur komplexieren Pyrogallol [4]arene größere Kationen, wie Tetramethylphosphonium, sogar stärker als die entsprechenden Resorcin [4]aren-Wirte. [230] ITC-Studien in Ethanol-Lösung (T = 298 K) zeigten, dass der Pyrogallol [4]aren-Wirt 22 (Abbildung 26 a) l-Carnitin (K a = (18 000 AE 1000) m À1 ) mit viel höherer Affinität als Betain (K a = (3200 AE 100) m À1 ), Cholin (K a = (3400 AE 200) m À1 ) und ACh (K a = (6100 AE 200) m À1 ) komplexiert. [225c] Die Bindung all dieser Gäste verläuft enthalpiegetrieben, einhergehend mit einem leichten Entropieverlust.…”

Section: Modellsystemeunclassified

Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen

2011

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Dieser Aufsatz beschreibt Phänomene der molekularen Erkennung von aromatischen Ringen in chemischen und biologischen Systemen in einem multidimensionalen Ansatz. Neue Ergebnisse aus der Wirt‐Gast‐Chemie, biologischen Affinitätsassays und Biostrukturanalysen, Datenbanksuchen in der Cambridge Structural Database (CSD) und der Protein Data Bank (PDB) und hochentwickelten Rechnungen, die seit dem Erscheinen eines früheren Aufsatzes in 2003 veröffentlicht wurden, sind hier zusammengefasst. Die Themen Aren‐Aren‐, Perfluoraren‐Aren‐, Schwefel‐Aren‐, Kation‐π‐ und Anion‐π‐Wechselwirkungen sowie Wasserstoffbrücken zu aromatischen Systemen werden behandelt. Das gewonnene Wissen kommt besonders der strukturbasierten Hit‐zur‐Leitstruktur‐Entwicklung und der Leitstrukturoptimierung sowohl in der pharmazeutischen als auch in der Pflanzenschutzindustrie zugute. Zudem erleichtert es die Entwicklung neuer Materialien und supramolekularer Systeme und soll zu weiteren Anwendungen von Wechselwirkungen mit aromatischen Ringen zur Kontrolle des stereochemischen Verlaufs chemischer Umsetzungen inspirieren.

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Section: Modellsystemeunclassified

Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen

2011

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“…[4][5][6][7] The bowl-shaped electron rich cavity of the C 4v of resorcinarenes and pyrogallarenes has been vastly explored in the binding of a variety of different guests through multiple weak interactions. [8][9][10][11][12] The eight and twelve hydroxyl groups on the upper rim of the resorcinarenes and pyrogallarenes, respectively, play a key role in maintaining their conformation. 13 These hydroxyl groups also aid the formation of many supramolecular assemblies and in co-crystallization studies.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

2015

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The binding of different categories of alkyl ammonium (secondary and tertiary mono-and diammonium) salts by resorcinarenes and a pyrogallarene through weak interactions were analysed in all phases. 1 H NMR spectroscopy and electrospray ionisation mass spectrometry were utilized in analysing the complexes in solution and in the gas phase respectively. The 1 H NMR titration studies in methanol-d 4 reveal the association constants for the 1:1 complexes to vary according to the electronic properties of hosts as well as the size, geometric orientation and charge concentration of the guest cations with binding constants of up to 950 M -1 in some cases. Mass spectrometry reveals 1:1 monomeric and 1:2 dimeric complexes in the gas phase. Six co-crystals, three of which are dimeric host-guest capsular assemblies, two open inclusion complexes and a pseudocapsular methanol solvate were analysed in the solid state through single-crystal X-ray diffraction. The crystal structures confirm the complexes to be held together by multiple cation···π, CH···π and hydrogen bond interactions.

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“…2, 4 The C 4 v conformation of unfunctionalized resorcinarenes has a concave cavity suitable for binding a variety of guests through several weak interactions 1. 5 Supramolecular assemblies such as 1:1 open inclusion complexes,6, 7 dimeric5, 8, 9 and hexameric10–13 capsular assemblies, and nanotubes14,15 have been reported. The phenolic hydroxyl groups make the 2‐position of the benzene ring suitable for electrophilic substitution.…”

Section: Introductionmentioning

confidence: 99%

Recognition of N‐Alkyl and N‐Aryl Acetamides by N‐Alkyl Ammonium Resorcinarene Chlorides

Beyeh

Ala‐Korpi

Cetina

et al. 2014

Chemistry A European J

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N-alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures, whereas in the presence of small guests the self-included dimers spontaneously reorganize to 1:1 host-guest complexes. These host compounds show an interesting ability to bind a series of N-alkyl acetamide guests through intermolecular hydrogen bonds involving the carbonyl oxygen (C=O) atoms and the amide (NH) groups of the guests, the chloride anions (Cl(-)) and ammonium (NH2(+)) cations of the hosts, and also through CH⋅⋅⋅π interactions between the hosts and guests. The self-included and host-guest complexes were studied by single-crystal X-ray diffraction, NMR titration, and mass spectrometry.

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Encapsulation of tetramethylphosphonium cations

Cited by 26 publications

References 21 publications

Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen

Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

Recognition of N‐Alkyl and N‐Aryl Acetamides by N‐Alkyl Ammonium Resorcinarene Chlorides

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