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Issue 11, 2009
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Predicting spontaneous racemate resolution using recent developments in crystal structure prediction

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Abstract

A hybrid molecular mechanics and quantum mechanics solid state DFT method is used to re-rank the stability of racemic and enantiopure crystal structures of four molecules; 4-hydroxymethyl-2-oxazolidinone, 5-hydroxymethyl-2-oxazolidinone, 2-(4-hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxy and 2-(3-hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxy. Previous work using a force field based method to predict these crystal structures indicated that the lattice energy may be a suitable criterion for predicting whether a chiral molecule will resolve spontaneously on crystallisation. However, in some cases, the method had predicted an unrealistically high lattice energy for the structure corresponding to the experimentally observed one. The Hybrid DFT method successfully predicts those molecules which resolve spontaneously and furthermore predicts satisfactory lattice energies for all experimentally observed structures. Based on a comparison of the predicted lattice energies from the two methods it is concluded that the force fields used were not sufficiently accurate to predict spontaneous resolution with any confidence. However, the Hybrid DFT method is shown to be sufficiently accurate for making such predictions.

Graphical abstract: Predicting spontaneous racemate resolution using recent developments in crystal structure prediction

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Publication details

The article was received on 06 May 2009, accepted on 29 Jun 2009 and first published on 24 Jul 2009


Article type: Paper
DOI: 10.1039/B909038J
Citation: CrystEngComm, 2009,11, 2391-2399
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    Predicting spontaneous racemate resolution using recent developments in crystal structure prediction

    J. Kendrick, M. D. Gourlay, M. A. Neumann and F. J. J. Leusen, CrystEngComm, 2009, 11, 2391
    DOI: 10.1039/B909038J

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