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N‐H⋅⋅⋅O, O‐H⋅⋅⋅O hydrogen bonded supramolecular formation in the cocrystal of salicylic acid with N‐containing bases
Author(s) -
Lee KyeongSill,
Kim KwangJoo,
Ulrich Joachim
Publication year - 2016
Publication title -
crystal research and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.377
H-Index - 64
eISSN - 1521-4079
pISSN - 0232-1300
DOI - 10.1002/crat.201500072
Subject(s) - cocrystal , salicylic acid , isonicotinamide , chemistry , benzoic acid , supramolecular chemistry , hydrogen bond , piperazine , synthon , crystal engineering , organic chemistry , medicinal chemistry , crystal structure , stereochemistry , molecule , biochemistry
Cocrystals of salicylic acid (derived from reaction between aspirin and coformers) with 4,4′dipyridyl, nicotinamide, isonicotinamide, N,N′‐diacetylpiperazine and piperazine have been examined with intent to improve physicochemical properties of antipyretic agent. All of the resulting cocrystals, salicylic acid/4,4′dipyridyl (2:1), salicylic acid/nicotinamide (1:1), salicylic acid/isonicotinamide (1:1), salicylic acid/piperazine (1:0.5) and salicylic acid/ N,N′‐diacetylpiperazine (2:1) (derived from reaction between aspirin and piperazine) are obtained solution cooling/evaporation experiments. The structural analysis has shown that the well‐known COOH ⋅⋅⋅ N heterosynthon was considered the key element in the cocrystals design strategy. The carboxylic acid ⋅⋅⋅ pyridine hydrogen bond is an often used supramolecular synthon. The results from X‐ray Powder Diffraction, DSC, Raman and single‐crystal X‐ray analysis revealed the formation of cocrystal of salicylic acid with several coformers.