Chiral Discrimination Mechanisms by Silylated-Acetylated Cyclodextrins: Superficial Interactions vs. Inclusion
Abstract
:1. Introduction
2. Results and Discussion
2.1. Conformation of the Cyclodextrin Derivatives
2.2. Enantiodiscrimination Processes by AcSiCDs
2.2.1. Compound B
2.2.2. Methyl 2-Chloropropionate
3. Materials and Methods
3.1. Materials
3.2. Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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CD | 1H NMR Analysis (OMe) | Diffusion Measurements | ||
---|---|---|---|---|
|δR − δSǀ | Δδ | xb | K | |
AcSiCD6 | 0 | 0.023 | 0.43 | 22.1 ± 7.9 |
AcSiCD7 | 0.026 | 0.089 (S) | 0.75 (S) | 78.8 ± 32.6 (S) |
0.063 (R) | 0.68 (R) | 55.1 ± 19.6 (R) | ||
AcSiCD8 | 0.101 | 0.250 (S) | n.d. 1 | n.d. 1 |
0.149 (R) | 0.64 (R) | 42.7 ± 13.7 (R) |
CD | 1H NMR Analysis (OMe) | Diffusion Measurements | ||
---|---|---|---|---|
|δR − δSǀ | Δδ | xb | K | |
AcSiCD6 | 0 | 0.002 | 0.03 | / |
AcSiCD7 | 0.096 | 0.151 (S) | 0.57 (S) | 92.8 ± 24.5 (S) |
0.054 (R) | 0.34 (R) | 30.6 ± 7.6 (R) | ||
AcSiCD8 | 0.020 | 0.089 (S) | 0.26 (S) | 20.6 ± 8.1 (S) |
0.069 (R) | 0.25 (R) | 19.0 ± 8.4 (R) |
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Balzano, F.; Uccello-Barretta, G.; Sicoli, G.; Vanni, L.; Recchimurzo, A.; Aiello, F. Chiral Discrimination Mechanisms by Silylated-Acetylated Cyclodextrins: Superficial Interactions vs. Inclusion. Int. J. Mol. Sci. 2022, 23, 13169. https://doi.org/10.3390/ijms232113169
Balzano F, Uccello-Barretta G, Sicoli G, Vanni L, Recchimurzo A, Aiello F. Chiral Discrimination Mechanisms by Silylated-Acetylated Cyclodextrins: Superficial Interactions vs. Inclusion. International Journal of Molecular Sciences. 2022; 23(21):13169. https://doi.org/10.3390/ijms232113169
Chicago/Turabian StyleBalzano, Federica, Gloria Uccello-Barretta, Giuseppe Sicoli, Letizia Vanni, Alessandra Recchimurzo, and Federica Aiello. 2022. "Chiral Discrimination Mechanisms by Silylated-Acetylated Cyclodextrins: Superficial Interactions vs. Inclusion" International Journal of Molecular Sciences 23, no. 21: 13169. https://doi.org/10.3390/ijms232113169