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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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Article information


Submitted
06 May 2009
Accepted
29 Jun 2009
First published
24 Jul 2009

CrystEngComm, 2009,11, 2391-2399
Article type
Paper

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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