Highly Polymorphous Nicotinamide and Isonicotinamide: Solution versus Melt Crystallization

Noalle Fellah, Carolyn Jin Zhang, Catherine Chen, Chunhua T. Hu, Bart Kahr, Michael D. Ward, Alexander G. Shtukenberg

Research output: Contribution to journalArticlepeer-review


The crystallization of nicotinamide (NA) and its constitutional isomer, isonicotinamide (INA), is compared. NA formed eight polymorphs from the melt and two from solution, whereas INA formed two polymorphs from the melt and six from solution. This analysis was provoked by the observation that NA is highly polymorphic from the melt, while the closely related INA is highly polymorphous from solution. A combination of hot stage polarized light microscopy, powder X-ray diffraction, and Raman spectroscopy revealed that the polymorph selectivities are not related to supramolecular self-association in the growth media. The larger estimated free energy gap separating NA polymorphs, compared with that of the INA polymorphs, is consistent with the smaller number of NA polymorphs generated from solution. Phenomenological analyses of crystallization kinetics suggest that cross nucleation is the most likely reason more polymorphs of NA than INA crystallize from the melt.

Original languageEnglish (US)
Pages (from-to)4713-4724
Number of pages12
JournalCrystal Growth and Design
Issue number8
StatePublished - Aug 4 2021

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics


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