An evidence for the chiral discrimination of naproxen enantiomers: A combined experimental and theoretical study

Yanli Wei, Sufang Wang, Jianbin Chao, Songbai Wang, Chuan Dong*, Shaomin Shuang, Man Chin Paau, Martin M F CHOI

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4033-4040
Number of pages8
JournalJournal of Physical Chemistry C
Volume115
Issue number10
DOIs
Publication statusPublished - 17 Mar 2011

Scopus Subject Areas

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films

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