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Progressive Folding and Adaptive Multivalent Recognition of Alkyl Amines and Amino Acids in p ‐Sulfonatocalix[4]arene Hosts: Solid‐State and Solution Studies
- Source :
- ChemPlusChem, ChemPlusChem, Wiley, 2020, 85 (8), pp.1623-1631. ⟨10.1002/cplu.202000232⟩, ChemPlusChem, Wiley, 2020, 85 (8), pp.1615-1615. ⟨10.1002/cplu.202000433⟩
- Publication Year :
- 2020
- Publisher :
- Wiley, 2020.
-
Abstract
- International audience; Calix[4]arenes have the ability to encapsulate biomimetic guests, offering interesting opportunities to explore their molecular recognition, very close to biological scenarios. In this study, p-sulfonatocalix[4]arene (C4 A) anions and hydrated alkali cations have been used for the in situ recognition of cationic 1,ω-diammonium-alkanes and 1,ω-amino-acids of variable lengths. NMR spectroscopy illustrates that these systems are stable in aqueous solution and the interaction process involves several binding states or stabilized conformations within the C4 A anion, depending of the nature of the guest. DOSY experiments showed that monomeric 1 : 1 host-guest species are present, while the cation does not influence their selfassembly in solution. The folded conformations observed in the solid-state X-ray single-crystal structures shed light on the constitutional adaptivity of flexible chains to environmental factors. Futhermore, a comprehensive screening of 30 single crystal structures helped to understand the in situ conformational fixation and accurate determination of the folded structures of the confined guest molecules, with a compression up to 40 % compared with their linear conformations.
- Subjects :
- chemistry.chemical_classification
Aqueous solution
010405 organic chemistry
Hydrogen bond
macromolecular substances
General Chemistry
Nuclear magnetic resonance spectroscopy
010402 general chemistry
01 natural sciences
0104 chemical sciences
Folding (chemistry)
Crystallography
Molecular recognition
chemistry
Calixarene
[CHIM]Chemical Sciences
Molecule
ComputingMilieux_MISCELLANEOUS
Alkyl
Subjects
Details
- ISSN :
- 21926506
- Volume :
- 85
- Database :
- OpenAIRE
- Journal :
- ChemPlusChem
- Accession number :
- edsair.doi.dedup.....5f0a61beee0244ede0638aabf0ea42ad