Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine
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 mech...
| Main Authors: | , , |
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| Format: | Journal Article |
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Springer-Verlag 2007
2012
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| Online Access: | http://hdl.handle.net/20.500.11937/38423 |
| _version_ | 1848755316786724864 |
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| author | Carter, Damien Kahr, B. Rohl, Andrew |
| author_facet | Carter, Damien Kahr, B. Rohl, Andrew |
| author_sort | Carter, Damien |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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 Ī 0) and ( Ī 1 0) surfaces. The aim is to develop a robust computational methodology that can be applied to understanding crystal-biased asymmetric synthesis. |
| first_indexed | 2025-11-14T08:54:22Z |
| format | Journal Article |
| id | curtin-20.500.11937-38423 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:54:22Z |
| publishDate | 2012 |
| publisher | Springer-Verlag 2007 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-384232017-09-13T16:01:26Z Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine Carter, Damien Kahr, B. Rohl, Andrew 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 Ī 0) and ( Ī 1 0) surfaces. The aim is to develop a robust computational methodology that can be applied to understanding crystal-biased asymmetric synthesis. 2012 Journal Article http://hdl.handle.net/20.500.11937/38423 10.1007/s00214-012-1125-y Springer-Verlag 2007 restricted |
| spellingShingle | Carter, Damien Kahr, B. Rohl, Andrew Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine |
| title | Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine |
| title_full | Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine |
| title_fullStr | Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine |
| title_full_unstemmed | Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine |
| title_short | Computational methodology for chirality determination in the Soai reaction by crystals: γ-glycine |
| title_sort | computational methodology for chirality determination in the soai reaction by crystals: γ-glycine |
| url | http://hdl.handle.net/20.500.11937/38423 |