Search
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.
Citations
-
1 9
CrossRef
-
0
Web of Science
-
2 1
Scopus
Cite as
Full text
full text is not available in portal
Keywords
Details
- Category:
- Magazine publication
- Type:
- Magazine publication
- Published in:
-
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
no. 85,
pages 132 - 140,
ISSN: 0928-0987 - ISSN:
- 0928-0987
- Publication year:
- 2016
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.ejps.2016.02.010
- Verified by:
- No verification
seen 131 times
Recommended for you
Exploring the cocrystallization potential of urea and benzamide
- P. Cysewski,
- M. Przybyłek,
- D. Ziółkowska
- + 1 authors
Utilization of oriented crystal growth for screening of aromatic carboxylic acids cocrystallization with urea
- M. Przybyłek,
- D. Ziółkowska,
- M. Kobierski
- + 2 authors
Applicability of phenolic acids as effective enhancers of cocrystals solubility of methylxanthines
- M. Przybyłek,
- D. Ziółkowska,
- K. Mroczyńska
- + 1 authors