Complete Deracemization by Attrition‐Enhanced Ostwald Ripening Elucidated
2008; Wiley; Volume: 120; Issue: 34 Linguagem: Inglês
10.1002/ange.200801846
ISSN1521-3757
AutoresWim L. Noorduin, Hugo Meekes, W.J.P. van Enckevort, Alessia Millemaggi, Michel Leeman, Bernard Kaptein, Richard M. Kellogg, Elias Vlieg,
Tópico(s)Photoreceptor and optogenetics research
ResumoAngewandte ChemieVolume 120, Issue 34 p. 6545-6547 Zuschrift Complete Deracemization by Attrition-Enhanced Ostwald Ripening Elucidated† Wim L. Noorduin, Wim L. Noorduin IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this authorHugo Meekes Dr., Hugo Meekes Dr. IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this authorWillem J. P. van Enckevort Dr., Willem J. P. van Enckevort Dr. IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this authorAlessia Millemaggi, Alessia Millemaggi Innovative Synthesis & Catalysis, DSM Pharmaceutical Products, PO Box 18, 6160 MD Geleen (The Netherlands), Fax: (+31) 46-476-7604Search for more papers by this authorMichel Leeman, Michel Leeman Syncom BV, Kadijk 3, 9747 AT Groningen (The Netherlands), Fax: (+31) 50-575-399Search for more papers by this authorBernard Kaptein Dr., Bernard Kaptein Dr. [email protected] Innovative Synthesis & Catalysis, DSM Pharmaceutical Products, PO Box 18, 6160 MD Geleen (The Netherlands), Fax: (+31) 46-476-7604Search for more papers by this authorRichard M. Kellogg Prof. Dr., Richard M. Kellogg Prof. Dr. [email protected] Syncom BV, Kadijk 3, 9747 AT Groningen (The Netherlands), Fax: (+31) 50-575-399Search for more papers by this authorElias Vlieg Prof. Dr., Elias Vlieg Prof. Dr. [email protected] IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this author Wim L. Noorduin, Wim L. Noorduin IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this authorHugo Meekes Dr., Hugo Meekes Dr. IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this authorWillem J. P. van Enckevort Dr., Willem J. P. van Enckevort Dr. IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this authorAlessia Millemaggi, Alessia Millemaggi Innovative Synthesis & Catalysis, DSM Pharmaceutical Products, PO Box 18, 6160 MD Geleen (The Netherlands), Fax: (+31) 46-476-7604Search for more papers by this authorMichel Leeman, Michel Leeman Syncom BV, Kadijk 3, 9747 AT Groningen (The Netherlands), Fax: (+31) 50-575-399Search for more papers by this authorBernard Kaptein Dr., Bernard Kaptein Dr. [email protected] Innovative Synthesis & Catalysis, DSM Pharmaceutical Products, PO Box 18, 6160 MD Geleen (The Netherlands), Fax: (+31) 46-476-7604Search for more papers by this authorRichard M. Kellogg Prof. Dr., Richard M. Kellogg Prof. Dr. [email protected] Syncom BV, Kadijk 3, 9747 AT Groningen (The Netherlands), Fax: (+31) 50-575-399Search for more papers by this authorElias Vlieg Prof. Dr., Elias Vlieg Prof. Dr. [email protected] IMM Solid State Chemistry, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen (The Netherlands), Fax: (+31) 24-365-3067Search for more papers by this author First published: 04 August 2008 https://doi.org/10.1002/ange.200801846Citations: 34 † We acknowledge Prof. D. G. Blackmond for the stimulating discussions. The SNN agency (Cooperation Northern Netherlands) and the European Fund for Regional Development (EFRO) are acknowledged for financial support. Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Geschüttelt und gerührt: Die Entstehung einer einheitlichen Chiralität im Festzustand beim Vermahlen einer Aufschlämmung wurde am Beispiel eines Phenylglycinamids kinetisch untersucht (siehe Schema). Die Ergebnisse geben Einblick in den zugrundeliegenden Prozess der abriebverstärkten Ostwald-Reifung, woraus optimale Reaktionsbedingungen zur Beschleunigung der Deracemisierung abgeleitet wurden. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description ange_200801846_sm_miscellaneous_information.pdf115.6 KB miscellaneous information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1H. Murakami, Top. Curr. Chem. 2007, 269, 273. 10.1007/128_2006_072 CASPubMedWeb of Science®Google Scholar 2J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolution, Krieger, Florida, 1994. Google Scholar 3L. Addadi, Z. Berkovitch-Yellin, N. Domb, E. Gati, M. Lahav, L. Leiserowitz, Nature 1982, 296, 21. 10.1038/296021a0 CASWeb of Science®Google Scholar 4L. Addadi, S. Weinstein, E. Gati, I. 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Google Scholar 22Throughout the paper we express amounts in terms of molalities (mol per kg solvent). Google Scholar 23A. E. Nielsen, O. Söhnel, J. Cryst. Growth 1971, 11, 233. 10.1016/0022-0248(71)90090-X CASWeb of Science®Google Scholar 24H. Briesen, Powder Technol. 2007, 178, 87–98. 10.1016/j.powtec.2007.04.011 CASWeb of Science®Google Scholar 25The linearity of the relationship between the solution racemization time and the DBU concentration was also checked (Supporting Information). Google Scholar 26The computer simulations show a minimum in the deracemization time as a function of the attrition probability ζ, which was found at high attrition rates, for which the CSD is dominated by the minimal crystal size that can be obtained by attrition (Supporting Information). Google Scholar 27Starting with ee(t=0)≠0 also suppresses stochastic behavior at low ee values.[20] Google Scholar 28As expected from Equation (3), scaling up of all parameters in the experiment has no influence on the deracemization rate. This was verified by performing experiments at a five times larger scale (ca. 20 g (R,S)-1, 0.25 mol kg−1 DBU, 50 g glass beads, 175 g MeCN). The enantiopure end state was again reached in 7 days (cf. Figure 1). Google Scholar Citing Literature Volume120, Issue34August 11, 2008Pages 6545-6547 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
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