Pasteur made simple – mechanochemical transformation of racemic amino acid crystals into racemic conglomerate crystals

Viedma, Cristóbal; Lennox, Cameron; Cuccia, Louis A.; Cintas, Pedro; Ortíz, José E.

doi:10.1039/c9cc10047d

Cited by 9 publications

(10 citation statements)

References 30 publications

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“…In some cases phases are produced such that are metastable in the form of coarse particles and stable when their particles are smaller than a certain size; their free energy is mainly contributed by the surface and surface structure [86][87][88]. The mechanical treatment of the pulp can give rise to violations of Ostwald's step rule [89] and the separation of optical isomer crystals [90][91][92]. Electrochemical potentials change; for example, gold can be oxidized by carbon dioxide [93].…”

Section: Inorganic Materials and Nanomaterialsmentioning

confidence: 99%

Role of Mixing and Milling in Mechanochemical Synthesis (Review)

Лапшин

Болдырева

Болдырев

2021

Russ. J. Inorg. Chem.

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Selected topics of inorganic mechanochemical synthesis are discussed. Variant mechanochemical syntheses are considered. The ex situ and in situ/operando methods to monitor the process are discussed. Methods for controlling the yield and kinetics of the mechanochemical synthesis are considered. The challenges and possible ways to address them are discussed. Thermal and mechanochemical syntheses are compared, with a special focus on mixing and milling processes. We consider the effects of various types of mechanical treatment on individual particles and on their mixtures. A special attention is paid to the macrokinetics of mechanochemical synthesis and its role in mixing and milling. The basic assumptions that render a mathematical model capable of describing the macrokinetics of mechanochemical synthesis in solid + reactive gas and solid + solid systems are written.

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Section: Inorganic Materials and Nanomaterialsmentioning

confidence: 99%

Role of Mixing and Milling in Mechanochemical Synthesis (Review)

Лапшин

Болдырева

Болдырев

2021

Russ. J. Inorg. Chem.

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“…For example, Shemchuk et al studied and summarized the ionic cocrystal structures between metal inorganic salt coformers and d l -amino acids. As a result, LiCl forms new ionic cocrystals with dl -leucine, dl -valine, and dl -alanine, while Li + and Zn 2+ form enantiopure cocrystals with dl -alloisoleucine and dl -proline. , Prof. Viedma demonstrated that dl -valine, dl -leucine, and dl -isoleucine can be converted to conglomerates by grinding/slurry conversion experiments with Zn/ZnO . These studies provide us with more enantioseparation methods.…”

Section: Introductionmentioning

confidence: 80%

“…13,14 Prof. Viedma demonstrated that DL-valine, DL-leucine, and DL-isoleucine can be converted to conglomerates by grinding/slurry conversion experiments with Zn/ZnO. 15 These studies provide us with more enantioseparation methods. However, so far, the mechanism of a coformer inducing chirality preference and resolution has not been completely understood.…”

Section: ■ Introductionmentioning

confidence: 99%

Thermodynamic and Molecular Recognition Mechanism of Diastereomeric Salt/Cocrystal-Induced Chiral Separation

Sui

Wang

et al. 2022

Crystal Growth & Design

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To better understand the thermodynamics and molecular self-assembly mechanism of diastereomeric salt/cocrystalinduced chiral separation, a series of 1:1 cocrystals and salts consisting of chiral valines (VAL) and tartaric acid derivatives were synthesized via different methods. Powders of these as-screened cocrystals/salts were characterized by PXRD, TGA, DSC, FT-IR, and Raman spectroscopy. The crystal structures of the five cocrystals/salts were determined and analyzed. It was found that both DBTA and DTTA form diastereomeric salt pairs with VAL enantiomers. Interestingly, L-DMTA cocrystallizes with D-VAL and L-VAL via hydrogen bonding and proton transfer, respectively. Considering this particularity, the differential isothermal (10 °C) ternary phase diagrams (TPDs) of D-DMTA and L-VAL (D-VAL) cocrystals (salt) were constructed in the mixed solvent of MeOH/ H 2 O. Moreover, a pure L-VAL:D-DMTA cocrystal and D-VAL:D-DMTA:0.5CH 4 O:0.25H 2 O salt were prepared via equimolar slurry conversion at 10 °C. In situ Raman spectroscopy was applied to monitor the molecular assembly process during the incubation of the cocrystal/salt. Molecular dynamics simulation was employed to rationalize the molecular recognition mechanism, demonstrating the excellent chirality preference of L-DMTA toward L-VAL instead of D-VAL. Calculations of density functional theory approved the synergistic instead of antagonistic effects of binding energy and solvation free energy toward chiral separation.

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“…384 Furthermore, a promising mechanochemical method to transform racemic compounds of amino acids into their corresponding conglomerates has been recently found. 385 When valine, leucine and isoleucine were milled one hour in the solid state, in a Teflon jar with a zirconium ball and in the decisive presence of zinc oxide, their corresponding conglomerates eventually formed. Shortly after the discovery of Viedma, aspartic acid 386 and glutamic acid 387,388 were deracemized up to homochiral state starting from biased racemic mixtures.…”

Section: 363mentioning

confidence: 99%