Linear deracemization kinetics during Viedma ripening: autocatalysis overruled by chiral additives

René R E Steendam, Janneke Dickhout, Willem J P Van Enckevort, Hugo Meekes, Jan Raap, Floris P J T Rutjes, Elias Vlieg

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Viedma ripening proceeds through an autocatalytic feedback mechanism which exponentially deracemizes an initially racemic solid state to an enantiopure end state. Here we show that, in the presence of enantiopure additives with a concentration of as low as 2.5 × 10-2 mol %, Viedma ripening proceeds with an overall linear and faster increase in enantiomeric excess. These experimental results can be explained using a simple model which assumes a difference in growth and dissolution rates between the enantiomers. This model also accounts for the generally observed linearity during the initial stages of Viedma ripening without additives.

LanguageEnglish
Pages1975-1982
Number of pages8
JournalCrystal Growth and Design
Volume15
Issue number4
Early online date3 Mar 2015
DOIs
Publication statusPublished - 1 Apr 2015

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autocatalysis
Kinetics
Enantiomers
enantiomers
kinetics
linearity
dissolving
Dissolution
solid state
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Keywords

  • linear deracemization kinetics
  • Viedma ripening
  • autocatalysis
  • chiral additives

Cite this

Steendam, R. R. E., Dickhout, J., Van Enckevort, W. J. P., Meekes, H., Raap, J., Rutjes, F. P. J. T., & Vlieg, E. (2015). Linear deracemization kinetics during Viedma ripening: autocatalysis overruled by chiral additives. Crystal Growth and Design , 15(4), 1975-1982. https://doi.org/10.1021/acs.cgd.5b00127
Steendam, René R E ; Dickhout, Janneke ; Van Enckevort, Willem J P ; Meekes, Hugo ; Raap, Jan ; Rutjes, Floris P J T ; Vlieg, Elias. / Linear deracemization kinetics during Viedma ripening : autocatalysis overruled by chiral additives. In: Crystal Growth and Design . 2015 ; Vol. 15, No. 4. pp. 1975-1982.
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Steendam, RRE, Dickhout, J, Van Enckevort, WJP, Meekes, H, Raap, J, Rutjes, FPJT & Vlieg, E 2015, 'Linear deracemization kinetics during Viedma ripening: autocatalysis overruled by chiral additives' Crystal Growth and Design , vol. 15, no. 4, pp. 1975-1982. https://doi.org/10.1021/acs.cgd.5b00127

Linear deracemization kinetics during Viedma ripening : autocatalysis overruled by chiral additives. / Steendam, René R E; Dickhout, Janneke; Van Enckevort, Willem J P; Meekes, Hugo; Raap, Jan; Rutjes, Floris P J T; Vlieg, Elias.

In: Crystal Growth and Design , Vol. 15, No. 4, 01.04.2015, p. 1975-1982.

Research output: Contribution to journalArticle

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AU - Steendam, René R E

AU - Dickhout, Janneke

AU - Van Enckevort, Willem J P

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AU - Vlieg, Elias

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AB - Viedma ripening proceeds through an autocatalytic feedback mechanism which exponentially deracemizes an initially racemic solid state to an enantiopure end state. Here we show that, in the presence of enantiopure additives with a concentration of as low as 2.5 × 10-2 mol %, Viedma ripening proceeds with an overall linear and faster increase in enantiomeric excess. These experimental results can be explained using a simple model which assumes a difference in growth and dissolution rates between the enantiomers. This model also accounts for the generally observed linearity during the initial stages of Viedma ripening without additives.

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Steendam RRE, Dickhout J, Van Enckevort WJP, Meekes H, Raap J, Rutjes FPJT et al. Linear deracemization kinetics during Viedma ripening: autocatalysis overruled by chiral additives. Crystal Growth and Design . 2015 Apr 1;15(4):1975-1982. https://doi.org/10.1021/acs.cgd.5b00127