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(2+3) amide cages by oxidation of (2+3) imine cages: revisiting molecular hosts for highly efficient nitrate binding

The pollution of groundwater with nitrate is a serious issue because nitrate can cause several diseases such as methemoglobinemia or cancer. Therefore, selective removal of nitrate by efficient binding to supramolecular hosts is highly desired. Here we describe how to make [2+3] amide cages in very...

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Main Authors: Lauer, Jochen (Author) , Bhat, Avinash S. (Author) , Barwig, Chantal (Author) , Fritz, Nathalie (Author) , Kirschbaum, Tobias (Author) , Rominger, Frank (Author) , Mastalerz, Michael (Author)
Format: Article (Journal)
Language:English
Published: September 12, 2022
In: Chemistry - a European journal
Year: 2022, Volume: 28, Issue: 51, Pages: 1-9
ISSN:1521-3765
DOI:10.1002/chem.202201527
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202201527
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202201527
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Author Notes:Jochen C. Lauer, Avinash S. Bhat, Chantal Barwig, Nathalie Fritz, Tobias Kirschbaum, Frank Rominger, and Michael Mastalerz
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Summary:The pollution of groundwater with nitrate is a serious issue because nitrate can cause several diseases such as methemoglobinemia or cancer. Therefore, selective removal of nitrate by efficient binding to supramolecular hosts is highly desired. Here we describe how to make [2+3] amide cages in very high to quantitative yields by applying an optimized Pinnick oxidation protocol for the conversion of corresponding imine cages. By NMR titration experiments of the eight different [2+3] amide cages with nitrate, chloride and hydrogen sulfate we identified one cage with an unprecedented high selectivity towards nitrate binding vs. chloride (S=705) or hydrogensulfate (S>13500) in CD2Cl2/CD3CN (1 : 3). NMR experiments as well as single-crystal structure comparison of host-guest complexes give insight into structure-property-relationships.
Item Description:Online veröffentlicht am 14. Juni 2022
Im Titel steht der Ausdruck "2+3" jeweils in eckiger Klammer
Gesehen am 08.12.2022
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202201527

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