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Exploring the crystal landscape of 3-methyl-2-phenylbutyramide: crystallization of metastable racemic forms from the stable conglomerate
Khandavilli, Udaya Bhaskara Rao
Gavin, Declan P.
Maguire, Anita R.
Lawrence, Simon E.
American Chemical Society (ACS)
In the solid state (±)-3-methyl-2-phenylbutyramide 1 spontaneously resolves into a conglomerate (Form I) that crystallizes in a racemic form (Form II) upon evaporation from the melt, a rarely reported phenomenon. An additional racemic polymorph, Form III, has been characterized, and the thermodynamic relationship between the three forms established by a variety of computational and experimental methods including grinding, slurry crystallization and seeding techniques. Both racemic Forms II and III are metastable and readily convert to the more stable conglomerate, Form I. Density Functional Theory calculations of the different polymorphs of 1 show that the enantiomers of 1 (R & S) are more stable than both racemic forms.
Conglomerate , Polymorphism , DFT calculations and crystallization , Density functional theory (DFT)
Khandavilli, U. B. R., Gavin, D., Maguire, A. R., Nolan, M. and Lawrence, S. E. (2018) 'Exploring the crystal landscape of 3-methyl-2-phenylbutyramide: crystallization of metastable racemic forms from the stable conglomerate', Crystal Growth & Design, doi: 10.1021/acs.cgd.8b00348
© American Chemical Society 2018. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth & Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.cgd.8b00348