A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+

Campayo, Lucrecia; Pardo, M.; Cotillas, Ana; Jaúregui, Oscar; Yunta, María J. R.; Cano, Carolina; Gómez-Contreras, Fernando; Navarro, Pilar; Sanz, A.

doi:10.1016/j.tet.2003.11.040

Cited by 8 publications

(3 citation statements)

References 32 publications

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“…Our research group has evaluated the possible cation-receptor interactions involved in the complexes with ammonium and metal cations of selective carriers using the Amber force field with appropriate parameters developed by us. The complexation energies obtained are in reasonable agreement with experimental values, taking into account that complexation/decomplexation processes have a great influence on transport rates and are not equally favoured in cyclic and acyclic carriers [Campayo et al, 2004].…”

Section: Selective Formation Of Complexessupporting

confidence: 83%

Using Molecular Modelling to Study Interactions Between Molecules with Biological Activity

Yunta¹

2012

Bioinformatics

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Section: Selective Formation Of Complexessupporting

confidence: 83%

Using Molecular Modelling to Study Interactions Between Molecules with Biological Activity

Yunta¹

2012

Bioinformatics

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“…Campayo et al examined acyclic compounds containing the 1,3-bis(6-oxopyridazin-1-yl)propane and the corresponding heteroaromatic macrocycles containing pyridine units [129] (Fig. 9).…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

214

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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“…In the development of artificial receptors, both macrocyclic 5a – g and acyclic compounds 4a , 6 , 7a – j , 8a b were considered. Among the acyclic compounds, tripodal 7a – e and hexapodal 8a b benzene derivatives with pyrazolyl or indazolyl groups, for example, were examined ( Figure 1b ).…”

Section: Introductionmentioning

confidence: 99%

Selective Recognition of Ammonium over Potassium Ion with Acyclic Receptor Molecules Bearing 3,4,5-Trialkylpyrazolyl Groups

2022

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Among the 1,3,5-trisubstituted 2,4,6-triethylbenzenes bearing pyrazolyl groups, the compounds with 3,5-dimethylpyrazolyl moieties were found to be effective receptors for ammonium ions (NH4+). The current study investigated the extent to which the incorporation of an additional alkyl group in the 4-position of the pyrazole ring affects the binding properties of the new compounds. 1H NMR spectroscopic titrations and investigations using isothermal titration calorimetry revealed that this small structural variation leads to a significant increase in the binding strength towards NH4+ and also improves the binding preference for NH4+ over K+. In addition to the studies in solution, crystalline complexes of the new triethyl- and trimethylbenzene derivatives, bearing 3,4,5-trialkylpyrazolyl groups, with NH4+PF6¯ were obtained and analyzed in detail. It is noteworthy that two of the crystal structures discussed in this work are characterized by the presence of two types of ammonium complexes. Studies focusing on the development of new artificial ammonium receptors are motivated, among other things, by the need for more selective ammonium sensors than those based on the natural ionophore nonactin.

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A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+

Cited by 8 publications

References 32 publications

Using Molecular Modelling to Study Interactions Between Molecules with Biological Activity

Using Molecular Modelling to Study Interactions Between Molecules with Biological Activity

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Selective Recognition of Ammonium over Potassium Ion with Acyclic Receptor Molecules Bearing 3,4,5-Trialkylpyrazolyl Groups

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