Department of Chemistry
An evidence for the chiral discrimination of naproxen enantiomers: A combined experimental and theoretical study
Naproxen enantiomers possess strong room temperature phosphorescence (RTP) in β-cyclodextrin (β-CD) system with a small amount of 1,2-dibromoethane (1,2-DBE) under ambient conditions. The effects of pH, concentration of β-CD, and 1,2-DBE on the RTP of naproxen enantiomers have been investigated in detail. Time-resolved RTP spectroscopy shows that both naproxen enantiomers exhibit biexponential decay pattern with lifetimes of τ1 = 4.79 ± 0.13 and τ2 = 1.51 ± 0.096 ms for R-naproxen and τ1 = 6.67 ± 0.15 and τ2 = 2.13 ± 0.061 ms for S-naproxen. The lifetime differences between these enantiomers are δτ1 = 1.88 and δτ2 = 0.62 ms, indicating that chiral discrimination of naproxen enantiomers can be achieved in β-CD/1,2-DBE system. Naproxen enantiomers can form stable complexes with β-CD and 1,2-DBE in stoichiometric ratios of 1:1:2 and 1:1:1 (naproxen:β-CD:1,2-DBE), and the association constants are 3.20 × 103 M-4 and 2.43 × 103 M-3 for the S- and R-enantiomers, respectively. The chiral discrimination of R-naproxen and S-naproxen is realized via their difference in interaction with the chiral cavity of β-CD due to their difference in stereochemical structure. Finally, molecular modeling is performed to determine the chiral recognition on a molecular level, and the results are in good agreement with the experimental data. © 2011 American Chemical Society.
Source Publication Title
Journal of Physical Chemistry C
American Chemical Society
Link to Publisher's Edition
Wei, Y., Wang, S., Chao, J., Wang, S., Dong, C., Shuang, S., Paau, M., & Choi, M. (2011). An evidence for the chiral discrimination of naproxen enantiomers: A combined experimental and theoretical study. Journal of Physical Chemistry C, 115 (10), 4033-4040. https://doi.org/10.1021/jp108464r