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 language | English (US) |
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Article number | 1125 |
Pages (from-to) | 1-7 |
Number of pages | 7 |
Journal | Theoretical Chemistry Accounts |
Volume | 131 |
Issue number | 2 |
DOIs | |
State | Published - Feb 2012 |
Keywords
- Crystal surfaces
- Enantioselectivity
- Molecular modelling
- Soai reaction
ASJC Scopus subject areas
- Physical and Theoretical Chemistry