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dc.contributor.authorGourlay, Matthew D.*
dc.contributor.authorKendrick, John*
dc.contributor.authorLeusen, Frank J.J.*
dc.date.accessioned2010-12-21T17:07:06Z
dc.date.available2010-12-21T17:07:06Z
dc.date.issued2008
dc.identifier.citationGourlay, M.D., Kendrick, J. and Leusen, F.J.J. (2008). Predicting the Spontaneous Chiral Resolution by Crystallization of a Pair of Flexible Nitroxide Radicals. Crystal Growth Design. Vol. 8, No. 8, pp. 2899-2905.en
dc.identifier.urihttp://hdl.handle.net/10454/4621
dc.descriptionNoen
dc.description.abstractThe separation of racemates into pure enantiomers through crystallization is an important industrial process. This study provides further validation of a novel, predictive approach for spontaneous resolution in which crystal structure prediction simulations are used to explore the relative stabilities of racemic solids versus enantiopure solids. 2-(4-Hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxy (compound 1) has previously been shown to be a racemic conglomerate, while a similar compound, 2-(3-hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxy (compound 2), was not. A conformational search using the Dreiding force field revealed 10 conformational minima for compound 1, and 20 for compound 2. Atomic charges were calculated using unrestricted DFT B3LYP 6-311G** optimized structures, and a crystal structure prediction was performed using the Dreiding force field, considering all low-energy gas-phase conformations and all relevant space groups. Analysis of the predicted crystal structures suggests that compound 1 is a racemic conglomerate, but compound 2 is not. This is in agreement with the experimental evidence.en
dc.language.isoenen
dc.relation.isreferencedbyhttp://dx.doi.org/10.1021/cg701256een
dc.subjectSpontaneous Chiral Resolutionen
dc.titlePredicting the Spontaneous Chiral Resolution by Crystallization of a Pair of Flexible Nitroxide Radicalsen
dc.status.refereedYesen
dc.typeArticleen
dc.type.versionNo full-text available in the repositoryen


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