Switching Polymorph Stabilities with Impurities: A Thermodynamic Route to Benzamide Form III

28 October 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We investigate the polymorphic behavior of benzamide, the first compound known to exhibit polymorphism, in the presence of small amounts of nicotinamide in the crystallization environment. A previous study by Emmerling et al.1 showed that the presence of nicotinamide promotes the transformation of the thermodynamic polymorph I of benzamide into its metastable polymorph III via mechanochemistry. We show that this transformation is the result of a thermodynamic switch between these two polymorphic forms driven by the formation of solid solutions with a small amount of nicotinamide. The presence of nicotinamide in the crystallization environment promotes the robust and exclusive crystallization of the elusive form III. These results represent a promising route to the synthesis and utilization of elusive polymorphs of pharmaceutical interest.

Keywords

polymorphism
solid solutions
benzamide form III
nicotinamide

Supplementary materials

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Kras-CruzCabeza Benzamide ESI
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