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

Damien J. Carter, Bart Kahr, Andrew L. Rohl

Research output: Contribution to journalArticle

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 1̄ 0) and (1̄ 1 0) surfaces. The aim is to develop a robust computational methodology that can be applied to understanding crystal-biased asymmetric synthesis.

Original languageEnglish (US)
Article number1125
Pages (from-to)1-7
Number of pages7
JournalTheoretical Chemistry Accounts
Volume131
Issue number2
DOIs
StatePublished - Feb 2012

Keywords

  • Crystal surfaces
  • Enantioselectivity
  • Molecular modelling
  • Soai reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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