Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 Dec 24;66(Pt 1):o226-7.
doi: 10.1107/S160053680905421X.

2-Propynyl 2-hydroxy-benzoate

Stephan M Levonis, Milton J Kiefel, Todd A Houston, Peter C Healy

2-Propynyl 2-hydroxy-benzoate

Stephan M Levonis et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound, C(10)H(8)O(3), has been synthesized as part of our investigations into the generation of new anti-bacterial agents and serves as a building block for the synthesis of compound libraries. The compound crystallizes with two independent mol-ecules in the asymmetric unit. The transoid propynyl ester groups are coplanar with the 2-hydroxy-benzoate group with maximum deviations of -0.3507 (3) and 0.1591 (3) Å for the terminal carbons, with intra-molecular O-H⋯O hydrogen bonding providing rigidity to the structure and ensuring that the reactivity of the alkyne is not compromised by steric factors. The propynyl group forms inter-molecular C-H⋯O inter-actions with the phenolic O atom. Supra-molecular chains along the b axis are found for both mol-ecules with links by weak O-H⋯O inter-molecular inter-actions in the first independent mol-ecule and C-H⋯O inter-actions in the second.

PubMed Disclaimer

Figures

Fig. 1.
Fig. 1.
Reaction scheme for the preparation of the title compound (I).
Fig. 2.
Fig. 2.
View of the two independent molecules in (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 40% probability level.
Fig. 3.
Fig. 3.
Crystal packing in the structure of (I), viewed down the c axis.
See this image and copyright information in PMC

References

    1. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
    1. Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
    1. Houston, T. A., Levonis, S. M. & Kiefel, M. J. (2007). Aust. J. Chem.60, 811–815.
    1. Houston, T. A., Quader, S., Boyd, S. E., Jenkins, I. D. & Healy, P. C. (2008). Acta Cryst. E64, o1738. - PMC - PubMed
    1. Houston, T. A., Wilkinson, B. L. & Blanchfield, J. T. (2004). Org. Lett.6, 678–681. - PubMed