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

doi:10.1021/jp108464r

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 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 language	English
Pages (from-to)	4033-4040
Number of pages	8
Journal	Journal of Physical Chemistry C
Volume	115
Issue number	10
DOIs	https://doi.org/10.1021/jp108464r
Publication status	Published - 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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@article{49c71892e31848f0ad5646dbc3a47fa6,

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

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.",

author = "Yanli Wei and Sufang Wang and Jianbin Chao and Songbai Wang and Chuan Dong and Shaomin Shuang and Paau, {Man Chin} and CHOI, {Martin M F}",

year = "2011",

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day = "17",

doi = "10.1021/jp108464r",

language = "English",

volume = "115",

pages = "4033--4040",

journal = "Journal of Physical Chemistry C",

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publisher = "American Chemical Society",

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T1 - An evidence for the chiral discrimination of naproxen enantiomers

T2 - A combined experimental and theoretical study

AU - Wei, Yanli

AU - Wang, Sufang

AU - Chao, Jianbin

AU - Wang, Songbai

AU - Dong, Chuan

AU - Shuang, Shaomin

AU - Paau, Man Chin

AU - CHOI, Martin M F

PY - 2011/3/17

Y1 - 2011/3/17

N2 - 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.

AB - 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.

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U2 - 10.1021/jp108464r

DO - 10.1021/jp108464r

M3 - Article

AN - SCOPUS:79953191150

SN - 1932-7447

VL - 115

SP - 4033

EP - 4040

JO - Journal of Physical Chemistry C

JF - Journal of Physical Chemistry C

IS - 10

ER -

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

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