[2+3] Amide Cages by Oxidation of [2+3] Imine Cages - Revisiting Molecular Hosts for Efficient Nitrate Binding [Data]

DOI

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 = 446) or hydrogensulfate (S >13000). NMR experiments as well as single-crystal structure comparison of host-guest complexes gave insight into structure property relationships.

Identifier
DOI https://doi.org/10.11588/data/HWLKZT
Related Identifier https://doi.org/10.1002/chem.202201527
Metadata Access https://heidata.uni-heidelberg.de/oai?verb=GetRecord&metadataPrefix=oai_datacite&identifier=doi:10.11588/data/HWLKZT
Provenance
Creator Lauer, Jochen C.; Bhat, Avinash S.; Barwig, Chantal; Rominger, Frank; Mastalerz, Michael
Publisher heiDATA
Contributor Mastalerz, Michael
Publication Year 2022
Rights CC BY 4.0; info:eu-repo/semantics/openAccess; http://creativecommons.org/licenses/by/4.0
OpenAccess true
Contact Mastalerz, Michael (Institute of Organic Chemistry, Heidelberg University)
Representation
Resource Type Dataset
Format application/zip
Size 64988223; 84412269; 78547787; 98070174; 84509616; 1203634; 94561126; 160112378; 276544702; 116630638; 172019361; 176658593; 153152473; 125672131; 306600816; 91354627; 103057395; 27603
Version 1.0
Discipline Chemistry; Natural Sciences