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oai:figshare.com:article/34021072 2026-09-29T04:05:04Z category_146 category_7 category_14 category_21 category_24 category_873 category_46 category_734 category_64 category_69 category_132 category_133 portal_63 item_type_6 month_year_09_2026

Dual-Selector Biphasic Recognition Chiral Extraction for Naproxen Enantiomers: Experimental Evaluation and Molecular-Level Mechanism Shuyuan Wen (25135078) Xiang Wei (1452547) Shengyuan Xu (543269) Hongye Cheng (1416415) Space Science Medicine Molecular Biology Biotechnology Evolutionary Biology Chemical Sciences not elsewhere classified Immunology Biological Sciences not elsewhere classified Cancer Inorganic Chemistry Infectious Diseases Plant Biology two selectors generate quantum chemical calculations opposite recognition preferences bonding network near phase chiral selectors preferred aqueous selector complementary organic selector molecular dynamics simulations modified cavity entrance cd preferentially stabilizes organic phase aqueous phase selector concentrations water interface tartaric acid steric complementarity size matching results indicate naproxen enantiomers level mechanism hydrophilic hydroxyethyl feed concentration experimental evaluation enantiomeric separations enantiomeric excess directional hydrogen di -< >- toluoyl >- naproxen 93 %. A dual-selector biphasic recognition chiral extraction (BRCE) system was developed for the resolution of racemic naproxen using hydrophobic l-di-<i>p</i>-toluoyl-d-tartaric acid (L-DTTA) in the organic phase and hydrophilic hydroxyethyl-β-cyclodextrin (HE-β-CD) in the aqueous phase. Single-selector screening first identified HE-β-CD as the preferred aqueous selector for <i>S</i>-naproxen and L-DTTA as a complementary organic selector for <i>R</i>-naproxen. After optimization of selector concentrations, feed concentration, pH and temperature, the single-stage enantioselectivity yields 2.10, with an enantiomeric excess of 31.93%. Quantum chemical calculations and molecular dynamics simulations were then used to interpret the experimentally verified selectivity trends. The results indicate that HE-β-CD preferentially stabilizes <i>S</i>-naproxen through cavity-size matching and a directional hydrogen-bonding network near the modified cavity entrance, whereas L-DTTA favors <i>R</i>-naproxen through steric complementarity and extensive van der Waals contacts. The opposite recognition preferences of the two selectors generate a cooperative thermodynamic driving force across the oil/water interface. This experimentally validated mechanism provides criteria for selecting dual-phase chiral selectors and designing intensified liquid–liquid extraction systems for enantiomeric separations. 2026-09-29T00:00:00Z Text Journal contribution 10.1021/acs.iecr.6c03193.s001 https://figshare.com/articles/journal_contribution/Dual-Selector_Biphasic_Recognition_Chiral_Extraction_for_Naproxen_Enantiomers_Experimental_Evaluation_and_Molecular-Level_Mechanism/34021072 CC BY-NC 4.0