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Record W4368372534 · doi:10.1021/acs.cgd.3c00364

Enhanced Direct Crystallization Resolution of Racemates Mediated in Chiral Ionic Liquid Cosolvent Mixtures: Experimental, Statistical, and QM Simulation Studies

2023· article· en· W4368372534 on OpenAlex
Xiaolan Qin, Yue Xu, Boxuan Lou, Chang Liu, Lijuan Zhang, Xijian Liu, Haikuan Yuan, Yan Zhang, Jie Lü

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueCrystal Growth & Design · 2023
Typearticle
Languageen
FieldChemical Engineering
TopicIonic liquids properties and applications
Canadian institutionsMemorial University of Newfoundland
FundersNational Natural Science Foundation of China
KeywordsChemistryIonic liquidNucleationCrystallizationEnantiomerYield (engineering)HomochiralityChirality (physics)Mole fractionRacemic mixtureEnantiomeric excessSolubilityCrystallographyPhysical chemistryOrganic chemistryEnantioselective synthesisThermodynamicsCatalysisChiral symmetry breaking

Abstract

fetched live from OpenAlex

Four chiral ionic liquids (CILs) of 1-hexyl-3-methylimidazolium- l -2-aminobutyrate ([Hmim][ l -2-AbA]), 1-hexyl-3-methylimidazolium- d -2-aminobutyrate ([Hmim][ d -2-AbA]), di-1-hexyl-3-methylimidazolium- l -malate ([Hmim] 2 [ l -MA]), and di-1-hexyl-3-methylimidazolium- d -malate ([Hmim] 2 [ d -MA]) were first prepared by a neutralization method and adequately characterized. In light of a gravimetric method, the molar fraction solubilities of dl - and d - together with l -threonine (Thr) were then acquired in the binary cosolvent mixtures (CM) of CILs and water, with different mass fractions (ω) of CILs under 101.3 kPa from 283.15 to 333.15 K. In CIL cosolvent mixtures (CCM), a cosolvency phenomenon was observed with the biggest solubilization and discrepant solubilities of Thr enantiomers, with ω of 0.3. Meanwhile, the asymmetry phenomenon was also found from the ternary phase diagram of Thr enantiomers and CCM, in which the enantiomeric excess values at the eutectic point (ee eut ) were sensitive to temperature. Subsequently, the nucleation experiments and appearance probability statistics confirmed that CCM with ω of 0.3 (CCM-0.3) can act as excellent nucleation inhibitors which preferred to suppress the nucleation of enantiomeric crystals with the opposite chirality to them, leading to the preferential nucleation of enantiomeric crystals with the same chirality. Furthermore, by coupling seeds and CCM-0.3, the yield and yield ratio of l -Thr products through a direct antisolvent crystallization resolution were improved greatly compared with that in water, where the largest yield ratio was up to 27.47%. At the same time, isosurface diagrams and binding energy calculations by quantum mechanics (QM) revealed that the higher chiral recognition ability of [Hmim] 2 [ l -MA] than [Hmim][ l -2-AbA] stemmed from the stronger weak interactions. Particularly, the enhanced direct crystallization resolution can be feasibly recycled owing to the stability and recyclability of the CILs.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.456
Threshold uncertainty score0.650

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.040
GPT teacher head0.300
Teacher spread0.260 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it