Synthesis of Diamido Bridged Homooxacalix[3]arenes and Their Recognition Property for Linear Alkylammonium Ions

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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“…Two typical examples have been described by Chen et al ( 95 ) [321] and Masci et al ( 96 ) [322] (Fig. 65).…”

Section: Reviewmentioning

confidence: 81%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

213

130

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“…Amido-di- O -bridged oxacalix[3]arenes were reported by Chen in 2005 through reaction of 3a with N , N’ -bis(chloroacetyl)-α,ω-alkylenediamines in refluxing acetone with K 2 CO 3 as the base (Scheme 16) [43–44]. Those compounds linked by two ( 28 ) or three ( 29 ) methylene groups had a binding affinity for linear primary alkyl ammonium ions from n -BuNH 3 + to n -HexNH 3 + .…”

Section: Reviewmentioning

confidence: 99%

“…Synthesis of strapped oxacalix[3]arene derivatives 28 and 29 : (i) N , N ’-Bis(chloroacetyl)-1,2-ethylenediamine or N , N ’-bis(chloroacetyl)-1,3-propylenediamine, K 2 CO 3 , acetone [43]. …”

Section: Reviewmentioning

confidence: 99%

Fifty years of oxacalix[3]arenes: A review

Cottet¹,

Marcos²,

Cragg³

2012

Beilstein J. Org. Chem.

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SummaryHexahomotrioxacalix[3]arenes, commonly called oxacalix[3]arenes, were first reported in 1962. Since then, their chemistry has been expanded to include numerous derivatives and complexes. This review describes the syntheses of the parent compounds, their derivatives, and their complexation behaviour towards cations. Extraction data are presented, as are crystal structures of the macrocycles and their complexes with guest species. Applications in fields as diverse as ion selective electrode modifiers, fluorescence sensors, fullerene separations and biomimetic chemistry are described.

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Functionalization and Properties of Homooxacalixarenes

Marcos

2016

Calixarenes and Beyond

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Synthesis of Diamido Bridged Homooxacalix[3]arenes and Their Recognition Property for Linear Alkylammonium Ions

Cited by 3 publications

References 22 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Fifty years of oxacalix[3]arenes: A review

Functionalization and Properties of Homooxacalixarenes

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