Abstract:
:A series of molecular complexes, both co-crystals and salts, of a triazole drug-alprazolam-with carboxylic acids, boric acid, boronic acids, and phenols have been analyzed with respect to heterosynthons present in the crystal structures. In all cases, the triazole ring behaves as an efficient hydrogen bond acceptor with the acidic coformers. The hydrogen bond patterns exhibited with aromatic carboxylic acids were found to depend on the nature and position of the substituents. Being a strong acid, 2,6-dihydroxybenzoic acid forms a salt with alprazolam. With aliphatic dicarboxylic acids alprazolam forms hydrates and the water molecules play a central role in synthon formation and crystal packing. The triazole ring makes two distinct heterosynthons in the molecular complex with boric acid. Boronic acids and phenols form consistent hydrogen bond patterns, and these are seemingly independent of the substitutional effects. Boronic acids form noncentrosymmetric cyclic synthons, while phenols form O--H...N hydrogen bonds with the triazole ring.
journal_name
J Pharm Scijournal_title
Journal of pharmaceutical sciencesauthors
Varughese S,Azim Y,Desiraju GRdoi
10.1002/jps.22117subject
Has Abstractpub_date
2010-09-01 00:00:00pages
3743-53issue
9eissn
0022-3549issn
1520-6017pii
S0022-3549(15)32474-6journal_volume
99pub_type
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