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Hydrophobic and Metal-Coordinated Confinement Effects Trigger Recognition and Selectivity
- Source :
- The Journal of Organic Chemistry. 86:8873-8881
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
Abstract
- We report the synthesis and characterization of a new water-soluble cavitand 1. The container features 2-aminobenzimidazole panels at the "rim" and pyridiniums at the "feet". In the solid state, a single-crystal X-ray structure of the organic-soluble precursor 2 showed a stable vase form. The structure is stabilized by hydrogen-bonded bridges between adjacent panels through solvents and ions. In aqueous solution, binding of hydrophobic and amphiphilic guest molecules to 1 was investigated using 1H NMR. Alkanes, alcohols, acids, diols, and diacids formed 1:1 host-guest complexes, and the guest conformations were deduced from characteristic chemical shift changes. In the presence of [Pd(ethylenediamine)(H2O)2·2NO3], cavitand 1 formed a complex incorporating two metals. The metal-coordinated cavitand also bound hydrophobic linear alkanes and difluorobenzene isomers in aqueous medium. The metallo-cavitand showed shape and size selectivity and was used to separate o-difluorobenzene from its isomers as observed by 19F NMR spectroscopy. The primary amino function of the cavitands offers possibilities for further elaboration to covalent clusters of these container compounds.
- Subjects :
- Models, Molecular
Magnetic Resonance Spectroscopy
Aqueous solution
010405 organic chemistry
Chemistry
Organic Chemistry
Molecular Conformation
Water
Cavitand
Ethylenediamine
010402 general chemistry
01 natural sciences
0104 chemical sciences
chemistry.chemical_compound
Covalent bond
Amphiphile
Polymer chemistry
Proton NMR
Molecule
Selectivity
Hydrophobic and Hydrophilic Interactions
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 86
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....bc058e89d78241d8578ebe06800f95b2