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Article
Propensity of salicylamide and ethenzamide cocrystallization with aromatic carboxylic acids
European Journal of Pharmaceutical Sciences (2016)
  • Maciej Przybyłek, Nicolaus Copernicus University of Torun
  • Dorota Ziółkowska, University of Technology and Life Sciences in Bydgoszcz
  • Karina Mroczyńska, University of Technology and Life Sciences in Bydgoszcz
  • Piotr Cysewski, Nicolaus Copernicus University of Torun
Abstract
The cocrystallization of salicylamide (2-hydroxybenzamide, SMD) and ethenzamide (2-ethoxybenzamide, EMD) with aromatic carboxylic acids was examined both experimentally and theoretically. The supramolecular synthesis taking advantage of the droplet evaporative crystallization (DEC) technique was combined with powder diffraction and vibrational spectroscopy as the analytical tools. This led to identification of eleven new cocrystals including pharmaceutically relevant coformers such as mono- and dihydroxybenzoic acids. The cocrystallization abilities of SMD and EMD with aromatic carboxylic acids were found to be unexpectedly divers despite high formal similarities of these two benzamides and ability of the R2,2(8) heterosynthon formation. The source of diversities of the cocrystallization landscapes is the difference in the stabilization of possible conformers by adopting alternative intramolecular hydrogen boding patterns. The stronger intramolecular hydrogen bonding the weaker affinity toward intermolecular complexation potential. The substituent effects on R2,2(8) heterosynthon properties are also discussed.
Keywords
  • Salicylamide,
  • Ethenzamide,
  • Pharmaceutical cocrystals,
  • Miscibility,
  • Aromatic carboxylic acids
Publication Date
2016
DOI
10.1016/j.ejps.2016.02.010
Citation Information
Maciej Przybyłek, Dorota Ziółkowska, Karina Mroczyńska and Piotr Cysewski. "Propensity of salicylamide and ethenzamide cocrystallization with aromatic carboxylic acids" European Journal of Pharmaceutical Sciences Vol. 85 (2016) p. 132 - 140
Available at: http://works.bepress.com/maciej-przybyek/19/