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2-bromoacetoxybenzoic acid, a brominated aspirin analog
P J Loll1, R M Garavito, C J Carrell
1Department of Biochemistry and Molecular Biology, University of Chicago, IL 60637, USA.
Acta Crystallographica. Section C, Crystal Structure Communications
|February 15, 1996
Summary
The crystal structure of 2-bromoacetoxybenzoic acid, a close analog of aspirin, reveals unique molecular twists and rotational disorder of the bromine atom. This finding offers insights into the structural variations of aspirin-like compounds.
Area of Science:
- Crystallography
- Organic Chemistry
- Medicinal Chemistry
Background:
- Aspirin (acetylsalicylic acid) is a widely used nonsteroidal anti-inflammatory drug.
- Understanding the structural nuances of aspirin analogs can inform drug design and development.
- 2-bromoacetoxybenzoic acid shares structural similarities with aspirin.
Purpose of the Study:
- To determine the crystal structure of 2-bromoacetoxybenzoic acid.
- To compare its structural features with those of aspirin.
- To investigate the molecular conformation and potential disorder within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed.
- The crystal structure was solved and refined.
- Molecular geometry and atomic positions were analyzed.
Main Results:
- The crystal structure of 2-bromoacetoxybenzoic acid (C9H7BrO4) was elucidated.
- A notable twist of 7.7(4) degrees was observed between the carboxylic acid moiety and the aromatic ring.
- The bromine atom exhibited rotational disorder, modeled across two sites with a 13(1) degree rotation.
Conclusions:
- 2-bromoacetoxybenzoic acid is a close structural analog of aspirin.
- The observed structural deviations, including carboxylic acid twisting and bromine atom disorder, provide valuable crystallographic data.
- These findings contribute to the understanding of structure-activity relationships in aspirin-like molecules.