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Peer-reviewedCC BY-NC 3.0RSC Advances

Probing the H-bonding features in [2.2.2]-cryptand/KF and permethylated β-cyclodextrin/KF complexed with protonated amino acids by 19F-NMR/IRMPD spectroscopy

  • So Yeon Lee1
  • Pengfei Xu2
  • Young-Ho Oh3
  • Hwa-Yong Jang1
  • Richard Brédy2
  • Isabelle Compagnon2
  • Han Bin Oh1
  • Sungyul Lee3
  1. 1Department of Chemistry, Sogang University Seoul 04107 Republic of Korea
  2. 2Université Lyon 1, CNRS, Institut Lumière Matière, UMR5306 Villeurbanne F-69100 France
  3. 3Department of Applied Chemistry, Kyung Hee University Gyeonggi 17104 Republic of Korea
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Abstract

We determined the configurations of [2.2.2]-cryptand/KF/protonated threonine ([222]/KF/ThrH+) and permethylated β-cyclodextrin/KF/AAH+ (perm-CD/KF/AAH+, AA = Thr, Trp, Ser) host–guest complexes in solution by examining the characteristic peak positions in the 19F-NMR spectra. We focused on which functional groups (ammonium, hydroxyl and carboxyl) in AAH+ form hydrogen bonds (H-bond) with F− and/or with the solvent. We observed strong dependence of the H-bonding features on the solvents. With no complex formed in D2O, the ammonium only binding to F− in ethylene glycol-d6, and the carboxyl forming H-bond with F− in CH3OH-d4. The structures of permethylated β-cyclodextrin/KF/AAH+ (perm-CD/AAH+; AA = Thr, Trp, Ser) in solution were also elucidated by 19F-NMR spectroscopy. The characteristic peaks observed at −178 ∼ −171 ppm signified that only the carboxyl group binds at the K+F− bridge. The IRMPD spectra were scrutinized for the perm-CD/KF/AAH+ adducts in the gas phase generated by the electrospray/mass spectroscopic (ESI/MS) procedure. By comparing the configurations of the host–guest complexes in the two distinct phases, we found that the identified gas-phase complexes were structurally similar to those in solution.

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Cite

BibTeXRIS
BibTeX
@article{lee2026probing,
  title = {{Probing the H-bonding features in [2.2.2]-cryptand/KF and permethylated β-cyclodextrin/KF complexed with protonated amino acids by 19F-NMR/IRMPD spectroscopy}},
  author = {So Yeon Lee and Pengfei Xu and Young-Ho Oh and Hwa-Yong Jang and Richard Brédy and Isabelle Compagnon and Han Bin Oh and Sungyul Lee},
  journal = {RSC Advances},
  year = {2026},
  month = nov,
  doi = {10.1039/d6ra06327f},
  url = {https://doi.org/10.1039/d6ra06327f},
  note = {CC BY-NC 3.0},
}
RIS
TY  - JOUR
TI  - Probing the H-bonding features in [2.2.2]-cryptand/KF and permethylated β-cyclodextrin/KF complexed with protonated amino acids by 19F-NMR/IRMPD spectroscopy
AU  - So Yeon Lee
AU  - Pengfei Xu
AU  - Young-Ho Oh
AU  - Hwa-Yong Jang
AU  - Richard Brédy
AU  - Isabelle Compagnon
AU  - Han Bin Oh
AU  - Sungyul Lee
PY  - 2026
DA  - 2026/11/04
JO  - RSC Advances
DO  - 10.1039/d6ra06327f
UR  - https://doi.org/10.1039/d6ra06327f
AB  - We determined the configurations of [2.2.2]-cryptand/KF/protonated threonine ([222]/KF/ThrH+) and permethylated β-cyclodextrin/KF/AAH+ (perm-CD/KF/AAH+, AA = Thr, Trp, Ser) host–guest complexes in solution by examining the characteristic peak positions in the 19F-NMR spectra. We focused on which functional groups (ammonium, hydroxyl and carboxyl) in AAH+ form hydrogen bonds (H-bond) with F− and/or with the solvent. We observed strong dependence of the H-bonding features on the solvents. With no complex formed in D2O, the ammonium only binding to F− in ethylene glycol-d6, and the carboxyl forming H-bond with F− in CH3OH-d4. The structures of permethylated β-cyclodextrin/KF/AAH+ (perm-CD/AAH+; AA = Thr, Trp, Ser) in solution were also elucidated by 19F-NMR spectroscopy. The characteristic peaks observed at −178 ∼ −171 ppm signified that only the carboxyl group binds at the K+F− bridge. The IRMPD spectra were scrutinized for the perm-CD/KF/AAH+ adducts in the gas phase generated by the electrospray/mass spectroscopic (ESI/MS) procedure. By comparing the configurations of the host–guest complexes in the two distinct phases, we found that the identified gas-phase complexes were structurally similar to those in solution.
SN  - 2046-2069
ER  -