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      Combining Viedma Ripening and Temperature Cycling Deracemization

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          Abstract

          While much data are available for the Viedma ripening and temperature cycling deracemization processes, not much is known about the advantages (or disadvantages) of a combination of the two. We here try to elucidate what happens when Viedma ripening is used in combination with temperature cycling by comparing not only the deracemization times but also the change in the sizes of the crystals. We found that, in the case of NMPA ( rac-(2-methylbenzylidene)-phenylglycine amide) as a model compound, combined experiments significantly increase the deracemization time. By tuning the process parameters, it is possible to approach experimental conditions where both Viedma ripening and temperature cycling control the deracemization. Under those conditions, however, the deracemization time is not significantly improved. Following our results, it seems unlikely that a combination of Viedma ripening and temperature cycling would shorten the deracemization time. Nevertheless, these experiments might provide clues for unraveling the mechanism of temperature cycling.

          Abstract

          For deracemization, temperature cycling (TC) is in general faster than Viedma ripening (VR). The combination of the two methods leads to intermediate deracemization times.

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          Most cited references31

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          Emergence of a single solid chiral state from a nearly racemic amino acid derivative.

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            Viedma ripening: a reliable crystallisation method to reach single chirality.

            Crystallisation processes have evolved to practical methods that allow isolation of an enantiopure product in high yield. Viedma ripening in particular enables access to enantiopure products in a reliable way, simply through grinding of crystals in a solution. This tutorial review covers the basic principles behind asymmetric crystallisation processes, with an emphasis on Viedma ripening, and shows that to date many novel organic molecules can be obtained in enantiopure solid form.
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              The Driving Mechanism Behind Attrition-Enhanced Deracemization

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                Author and article information

                Journal
                Cryst Growth Des
                Cryst Growth Des
                cg
                cgdefu
                Crystal Growth & Design
                American Chemical Society
                1528-7483
                1528-7505
                31 January 2022
                02 March 2022
                : 22
                : 3
                : 1874-1881
                Affiliations
                [1]Institute for Molecules and Materials, Radboud University , Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
                Author notes
                Author information
                https://orcid.org/0000-0001-9236-2129
                https://orcid.org/0000-0003-1538-3852
                https://orcid.org/0000-0002-1343-4102
                Article
                10.1021/acs.cgd.1c01423
                8895382
                8ab3ebf3-b06d-42d5-9f3b-7a11b9a9b009
                © 2022 The Authors. Published by American Chemical Society

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                : 02 December 2021
                : 14 January 2022
                Funding
                Funded by: H2020 Marie Sklodowska-Curie Actions, doi 10.13039/100010665;
                Award ID: 722456 CORE ITN
                Categories
                Article
                Custom metadata
                cg1c01423
                cg1c01423

                Materials technology
                Materials technology

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