Published October 2, 2003
| Supplemental Material
Journal Article
Open
Conformations of 2-Carboxy-1,4-butanedioic Acid as a Function of Ionization State in Dimethyl Sulfoxide
- Creators
- Nair, Gautham
- Roberts, John D.
Chicago
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Abstract
The conformational equilibria of 2-carboxy-1,4-butanedioic acid and its mono-, di-, and trianions were estimated by NMR couplings in dimethyl sulfoxide (DMSO). Intramolecular hydrogen bonding was inferred for the mono- and dianions, but not for the triacid. For the di- and trianions, the ^3/_(HH) couplings were consistent with the negative carboxylate groups being much closer together than might be expected from electrostatic repulsion considerations. The successive triacid pK_a values were estimated as 7.0, 13.4, and ∼20(?) on the Bordwell scale.
Additional Information
© 2003 American Chemical Society. Received July 22, 2003. Publication Date (Web): September 10, 2003. This work was supported by the donors of the Petroleum Research Fund, administered by the American Chemical Society, the Caltech Summer Undergraduate Research Fellowship Program (SURF), E. I. Du Pont Company, Dr. & Mrs. Chester M. McCloskey, the Camille and Henry Dreyfus Foundation, and Merck and Company. We greatly appreciate the assistance of Krag Petterson in many ways in this project.Attached Files
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Additional details
- Eprint ID
- 60651
- DOI
- 10.1021/ol030089o
- Resolver ID
- CaltechAUTHORS:20151001-101402532
- American Chemical Society Petroleum Research Fund
- Caltech Summer Undergraduate Research Fellowship (SURF)
- E. I. Du Pont Company
- Dr. and Mrs. Chester M. McCloskey
- Camille and Henry Dreyfus Foundation
- Merck and Company
- Created
-
2015-10-02Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field