Calix[4]arene phosphonates ‐ recognition of amino alcohols in water

Witt, Dariusz; Dziemidowicz, Joanna; Rachoń, Janusz

doi:10.1002/hc.10229

Cited by 23 publications

(10 citation statements)

References 16 publications

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“…Unfortunately, the 1:1 complexes are often insoluble in water and in some cases even precipitate from methanol. A calix[4]arene containing four phosphonate groups at the upper rim complexes the hydrochloride salts of (1 R ,2 S )‐(−)‐ephedrine, (1 R ,2 S )‐(−)‐norephedrine, ( R )‐(−)‐noradrenaline, and 2‐phenylethylamine 124. The binding constants for the 1:1 complexes vary from 45 M −1 to 145 M −1 in D 2 O buffered with 200 m M phosphate.…”

Section: Cyclophanesmentioning

confidence: 99%

Supramolecular Chemistry in Water

2007

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Supramolecular chemistry in water is a constantly growing research area because noncovalent interactions in aqueous media are important for obtaining a better understanding and control of the major processes in nature. This Review offers an overview of recent advances in the area of water-soluble synthetic receptors as well as self-assembly and molecular recognition in water, through consideration of the functionalities that are used to increase the water solubility, as well as the supramolecular interactions and approaches used for effective recognition of a guest and self-assembly in water. The special features and applications of supramolecular entities in aqueous media are also described.

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Section: Cyclophanesmentioning

confidence: 99%

Supramolecular Chemistry in Water

2007

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“…Witt et al researched the complexation properties of water-soluble calix[4]arenes based cavitands ( Fig. 61 ) with (1 R, 2 S )-(−)-ephedrine ( 79a ), (1 R ,2 S )-(−)-norephedrine ( 79b ), ( R )-(−)-noradrenaline hydrochloride ( 80b ) and 2-phenylethylamine hydrochloride ( 78a ) in phosphate buffer at pD 7.3 [ 302 ]. The host molecules were intended to mimic the adrenergic receptor.…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

220

130

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SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

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“…Allerdings sind die 1:1‐Komplexe oft in Wasser und gelegentlich sogar in Methanol unlöslich. Ein Calix[4]aren mit vier Phosphonatgruppen am oberen Rand komplexiert die Hydrochloride von (1 R ,2 S )‐(−)‐Ephedrin, (1 R ,2 S )‐(−)‐Norephedrin, ( R )‐(−)‐Noradrenalin und 2‐Phenylethylamin 124. Die Bindungskonstanten für die 1:1‐Komplexe in D 2 O mit 200 m M Phosphatpuffer variieren zwischen 45 M −1 und 145 M −1 .…”

Section: Cyclophaneunclassified

Self‐Discriminating Self‐Assembly of Dinuclear Heterochiral Rhombs from Tröger’s Base Derived Bis(pyridyl) Ligands

Weilandt

Kiehne

Bunzen

et al. 2010

Chemistry A European J

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Five racemic dissymmetric bis(pyridyl) ligands based on 2,8- or 3,9-difunctionalised Tröger's base derivatives have been synthesised. Only those derived from a 2,8-difunctionalised scaffold were found to undergo selective self-assembly to discrete self-assembled dinuclear metallosupramolecular aggregates of rhomboid shape upon coordination to cis-protected Pd(2+) or Pt(2+) ions, as evidenced by ESI mass spectrometry, NMR spectroscopy and single-crystal X-ray diffraction. Interestingly, these processes were found to be highly diastereoselective leading to the formation of C(2v)-symmetric heterochiral assemblies in a self-discriminating manner.

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Calix[4]arene phosphonates ‐ recognition of amino alcohols in water

Abstract: ABSTRACT:The water-soluble calix [4]

Cited by 23 publications

References 16 publications

Supramolecular Chemistry in Water

Supramolecular Chemistry in Water

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Self‐Discriminating Self‐Assembly of Dinuclear Heterochiral Rhombs from Tröger’s Base Derived Bis(pyridyl) Ligands

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