Enantioselective binding of additives to chiral crystals
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, thus our aim has been to develop a robust computational methodology that can be...
| Main Authors: | , , |
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| Format: | Conference Paper |
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AMER CHEMICAL SOC
2012
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| Online Access: | http://hdl.handle.net/20.500.11937/29620 |
| _version_ | 1848752853514977280 |
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| author | Carter, D. Kahr, B. Rohl, Andrew |
| author_facet | Carter, D. Kahr, B. Rohl, Andrew |
| author_sort | Carter, D. |
| 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, thus our aim has been to develop a robust computational methodology that can be applied to understanding crystal-biased asymmetric synthesis. Using a combination of forcefield-based calculations coupled with simulated annealing calculations, we have examined two model crystal systems - g-glycine and N-(2-thienylcarbonyl)glycine. The simulations provide binding energies of Soai reactant and product molecules on the exposed faces of the catalytic crystals. Using these energies, a Boltzmann distribution can predict the most abundant orientations of these molecules at each surface, and information regarding the final product can be derived. In the case of N-(2-thienylcarbonyl)glycine, this can be correlated with stereochemical outcomes of the Soai reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy. |
| first_indexed | 2025-11-14T08:15:13Z |
| format | Conference Paper |
| id | curtin-20.500.11937-29620 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:15:13Z |
| publishDate | 2012 |
| publisher | AMER CHEMICAL SOC |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-296202018-12-14T01:00:04Z Enantioselective binding of additives to chiral crystals Carter, D. 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, thus our aim has been to develop a robust computational methodology that can be applied to understanding crystal-biased asymmetric synthesis. Using a combination of forcefield-based calculations coupled with simulated annealing calculations, we have examined two model crystal systems - g-glycine and N-(2-thienylcarbonyl)glycine. The simulations provide binding energies of Soai reactant and product molecules on the exposed faces of the catalytic crystals. Using these energies, a Boltzmann distribution can predict the most abundant orientations of these molecules at each surface, and information regarding the final product can be derived. In the case of N-(2-thienylcarbonyl)glycine, this can be correlated with stereochemical outcomes of the Soai reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy. 2012 Conference Paper http://hdl.handle.net/20.500.11937/29620 AMER CHEMICAL SOC restricted |
| spellingShingle | Carter, D. Kahr, B. Rohl, Andrew Enantioselective binding of additives to chiral crystals |
| title | Enantioselective binding of additives to chiral crystals |
| title_full | Enantioselective binding of additives to chiral crystals |
| title_fullStr | Enantioselective binding of additives to chiral crystals |
| title_full_unstemmed | Enantioselective binding of additives to chiral crystals |
| title_short | Enantioselective binding of additives to chiral crystals |
| title_sort | enantioselective binding of additives to chiral crystals |
| url | http://hdl.handle.net/20.500.11937/29620 |