Theoretical Chemistry Accounts

, 131:1125

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

Regular Article

DOI: 10.1007/s00214-012-1125-y

Cite this article as:
Carter, D.J., Kahr, B. & Rohl, A.L. Theor Chem Acc (2012) 131: 1125. doi:10.1007/s00214-012-1125-y

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.

Keywords

Molecular modelling Soai reaction Crystal surfaces Enantioselectivity 

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Damien J. Carter
    • 1
    • 3
  • Bart Kahr
    • 2
  • Andrew L. Rohl
    • 1
    • 3
  1. 1.Department of Chemistry, Nanochemistry Research InstituteCurtin UniversityPerthAustralia
  2. 2.Department of ChemistryNew York UniversityNew YorkUSA
  3. 3.iVEC, Technology ParkKensingtonAustralia

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