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Hydrogen bonding of catechol groups in the crystal structure of dihydrocaffeic acid

Drebushchak, T.N.; Boldyreva, E.V.; Fucke, K.

Authors

T.N. Drebushchak

E.V. Boldyreva

K. Fucke



Abstract

Dihydrocaffeic acid C9H10O4 is a natural antioxidant. The crystal structure of dihydrocaffeic acid is determined; the crystallographic data at 100 K are: a = 11.3189(4) Å, b = 5.5824(1) Å, c = 13.8431(4) Å, β = 109.248(4)°, and V = 825.80(4) Å3; the space group is P21/c, Z = 4. In addition to the formation of hydrogen bonds that are typical of acids, the compound has features that are important from the viewpoint of reactivity of dihydrocaffeic acid molecules. The position of one of the hydroxyl hydrogen atoms in the catechol group is disordered even at 100 K. The crystal structure of caffeic acid does not show such a disordering.

Citation

Drebushchak, T., Boldyreva, E., & Fucke, K. (2013). Hydrogen bonding of catechol groups in the crystal structure of dihydrocaffeic acid. Journal of Structural Chemistry, 54(2), 368-372. https://doi.org/10.1134/s0022476613020133

Journal Article Type Article
Publication Date Mar 1, 2013
Deposit Date Jan 16, 2014
Journal Journal of Structural Chemistry
Print ISSN 0022-4766
Electronic ISSN 1573-8779
Publisher Springer
Peer Reviewed Peer Reviewed
Volume 54
Issue 2
Pages 368-372
DOI https://doi.org/10.1134/s0022476613020133
Keywords Catechol compounds, Hydrogen bonds, Dihydrocaffeic acid, Single-crystal X-ray diffraction.

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