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

Fingerprint

Chirality
glycine
chirality
Glycine
methodology
Crystals
Enantioselectivity
simulated annealing
Simulated annealing
Binding energy
organic compounds
Organic compounds
crystals
binding energy
Adsorption
adsorption
synthesis
interactions

Keywords

  • Crystal surfaces
  • Enantioselectivity
  • Molecular modelling
  • Soai reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Computational methodology for chirality determination in the Soai reaction by crystals : γ-glycine. / Carter, Damien J.; Kahr, Bart; Rohl, Andrew L.

In: Theoretical Chemistry Accounts, Vol. 131, No. 2, 02.2012, p. 1-7.

Research output: Contribution to journalArticle

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