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Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine

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Abstract

The autocatalytic Soai reaction gives abundant evidence of the enantioselective adsorption of organic compounds on a variety of crystals. Computational modelling can provide insight into mechanisms of enantioselectivity. Here, we use a combination of simulated annealing, forcefield, and quantum mechanical methods to examine interactions of pyrimidyl-5-carbaldehyde and 2-methylpyrimidyl-5-carbaldehyde with surfaces of γ-glycine. Using binding energy results, we predict the exposure of the pro-stereogenic S face of pyrimidyl-5-carbaldehyde (~65%) and 2-methylpyrimidyl-5-carbaldehyde (>90%) on the (1 \( \bar{1} \) 0) and (\( \bar{1} \) 1 0) surfaces. The aim is to develop a robust computational methodology that can be applied to understanding crystal-biased asymmetric synthesis.

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Acknowledgments

BK thanks the United States National Science Foundation (NSF) for support of this research. ALR and DJC acknowledge the National Computational Infrastructure (NCI) National Facility and iVEC for access to computational resources. We are grateful to John Freudenthal for his efforts to establish the absolute structure of the crystals of γ-glycine optically.

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Authors and Affiliations

  1. Department of Chemistry, Nanochemistry Research Institute, Curtin University, Perth, WA, Australia

    Damien J. Carter & Andrew L. Rohl

  2. Department of Chemistry, New York University, New York, NY, USA

    Bart Kahr

  3. iVEC, Technology Park, Kensington, WA, Australia

    Damien J. Carter & Andrew L. Rohl

Authors
  1. Damien J. Carter
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  2. Bart Kahr
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  3. Andrew L. Rohl
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Correspondence to Damien J. Carter.

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Carter, D.J., Kahr, B. & Rohl, A.L. Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine. Theor Chem Acc 131, 1125 (2012). https://doi.org/10.1007/s00214-012-1125-y

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