Journal article
Elusive Nonsolvated Cocrystals of Aspirin: Two Polymorphs with Bipyridine Discovered with the Assistance of Mechanochemistry
Crystal growth & design, Vol.18(4), pp.2495-2501
04/04/2018
DOI: 10.1021/acs.cgd.8b00104
Abstract
We report the discovery two nonsolvated polymorphic cocrystals of acetylsalicylic acid (ASA) and 4,4′-bipyridine (4,4′-bipy) in the form of 2(ASA)·(4,4′-bipy). Form I was discovered through mechanical dry grinding, and Form II was discovered through rapid cooling in ethanol. Both polymorphs consist of three-component hydrogen-bonded assemblies sustained by O-H···N hydrogen bonds. The components of the assemblies adopt an anti-conformation. The polymorphs differ in terms of relative twists of carboxylic acid groups and pyridyl rings. In Form I the ASA molecules are linked by discrete catemeric methyl C-H···O forces of the acetyl substituents, while in Form II the ASA molecules are linked by both infinite methyl C-H···O catemers and centrosymmetric dimers of the acetyl groups. Our results demonstrate the importance of neat mechanical grinding in the discovery and design of pharmaceutical cocrystals and polymorphs.
Details
- Title: Subtitle
- Elusive Nonsolvated Cocrystals of Aspirin: Two Polymorphs with Bipyridine Discovered with the Assistance of Mechanochemistry
- Creators
- Shalisa M Oburn - Department of Chemistry, University of Iowa, Iowa City, Iowa 52245-1297, United StatesOlivia A Ray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52245-1297, United StatesLeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52245-1297, United States
- Resource Type
- Journal article
- Publication Details
- Crystal growth & design, Vol.18(4), pp.2495-2501
- DOI
- 10.1021/acs.cgd.8b00104
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Grant note
- DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1708673
- Language
- English
- Date published
- 04/04/2018
- Academic Unit
- Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
- Record Identifier
- 9984216565202771
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