Abstract
Isotopic chirality influences sensitively the enantiomeric outcome of the Soai asymmetric autocatalysis. Therefore magnitude and eventual effects of isotopic chirality caused by natural abundance isotopic substitution (H, C, O, Zn) in the reagents of the Soai reaction were analyzed by combinatorics and probability calculations. Expectable enantiomeric excesses were calculated by the Pars–Mills equation. It has been found that the chiral isotopic species formed by substitution in the otherwise achiral reagents provide enantiomeric excess (e.e.) levels that are higher than the sensitivity threshold of the Soai autocatalysis towards chiral induction. Consequently, possible chiral induction exerted by these e.e. values should be taken into account in considerations regarding the molecular events and the mechanism of the chiral induction in the Soai reaction.
Highlights
Effects caused by isotopic substitution have been broadly investigated and applied in analytical, organic and biological chemistry [1,2,3,4,5,6,7]
These groups consist of H and C, the isotopic substitution by these elements iso-Pr group in compounds 2 and 3
These groups consist of H and C, the isotopic substitution by will be analyzed here
Summary
Effects caused by isotopic substitution have been broadly investigated and applied in analytical, organic and biological chemistry [1,2,3,4,5,6,7]. We calculated for compound S-E4, with the Pars–Mills Equation (with 50% confidence, see Supporting Materials 2) the expectable e.e.50% values from sample sizes ranging from millimol to femtomol, for the chiral fraction of the molecules (Table 3): Table 3.
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