Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis

Béla Barabás, Claudia Zucchi, Marco Maioli, K. Micskei, Gyula Pályi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Absolute asymmetric synthesis (AAS) is the preparation of pure (or excess of one) enantiomer of a chiral compound from achiral precursor(s) by a chemical reaction, without enantiopure chiral additive and/or without applied asymmetric physical field. Only one well-characterized example of AAS is known today: the Soai-autocatalysis. In an attempt at clarification of the mechanism of this particular reaction we have undertaken empirical and stochastic analysis of several parallel AAS experiments. Our results show that the initial steps of the reaction might be controlled by simple normal distribution (“coin tossing”) formalism. Advanced stages of the reaction, however, appear to be of a more complicated nature. Symmetric beta distribution formalism could not be brought into correspondence with the experimental observations. A bimodal beta distribution algorithm provided suitable agreement with the experimental data. The parameters of this bimodal beta function were determined by a Pólya-urn experiment (simulated by computer). Interestingly, parameters of the resulting bimodal beta function give a golden section ratio. These results show, that in this highly interesting autocatalysis two or even perhaps three catalytic cycles are cooperating. An attempt at constructing a “designed” Soai-type reaction system has also been made.

Original languageEnglish
JournalJournal of Molecular Modeling
Volume21
Issue number2
DOIs
Publication statusPublished - 2015

Fingerprint

autocatalysis
synthesis
Enantiomers
Normal distribution
formalism
Chemical reactions
enantiomers
Experiments
normal density functions
chemical reactions
preparation
cycles

Keywords

  • Absolute asymmetric synthesis
  • Asymmetric autocatalysis
  • Empirical models
  • Soai reaction
  • Stochastic models

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computer Science Applications
  • Computational Theory and Mathematics
  • Catalysis
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis. / Barabás, Béla; Zucchi, Claudia; Maioli, Marco; Micskei, K.; Pályi, Gyula.

In: Journal of Molecular Modeling, Vol. 21, No. 2, 2015.

Research output: Contribution to journalArticle

Barabás, Béla ; Zucchi, Claudia ; Maioli, Marco ; Micskei, K. ; Pályi, Gyula. / Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis. In: Journal of Molecular Modeling. 2015 ; Vol. 21, No. 2.
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