Solution conformational preferences of glutaric, 3-hydroxyglutaric, 3-methylglutaric acid, and their mono- and dianions
Abstract
Conformational preferences of glutaric, 3-hydroxyglutaric and 3-methylglutaric acid, and their mono- and dianions have been investigated with the aid of NMR spectroscopy. In contrast to succinic acid, glutaric acid displays essentially statistical conformational equilibria in polar and non-polar solutions of high and low hydrogen-bonding ability with no clear evidence for intramolecular hydrogen-bonding interactions. The acid ionization constant ratios, K_1/K_2, in D_2O and DMSO of glutaric, 3-hydroxyglutaric, and 3-methylglutaric acids also indicate that intramolecular interactions are much less important than, or indeed insignificant, for shorter-chain acids. FTIR studies on 3-methylglutaric acid indicate some preference for either association with solvent or dimerization, depending on the solvent, rather than intramolecular hydrogen bonding.
Additional Information
© 2008 John Wiley & Sons, Ltd. Received: 7 August 2007, Revised: 11 September 2007, Accepted: 15 September 2007, Article first published online: 15 Jan 2008. The donors of the Petroleum Research Fund administered by the American Chemical Society are acknowledged for their support of this research. This research is also based upon work supported by the National Science Foundation under Grant No.CHE-0543620, the Summer Undergraduate Research Fellowship Program (SURF) at the California Institute of Technology, and the Senior Scientist Mentor Program of the Camille and Henry Dreyfus Foundation. In addition, we are indebted to Merck & Company, Dr and Mrs Chester M. Mccloskey, Dr David J. Mathre, and Edith M. Roberts for their helpful financial assistance. The authors thank Scott Ross, Krag Petterson, and Diego Benftez Gutierrez for their kind help and Prof. Joseph Casanova and Robin Stein for helpful discussions.Additional details
- Eprint ID
- 60608
- Resolver ID
- CaltechAUTHORS:20150930-125950470
- American Chemical Society Petroleum Research Fund
- CHE-0543620
- NSF
- Caltech Summer Undergraduate Research Fellowship (SURF)
- Camille and Henry Dreyfus Foundation
- Merck & Company
- Dr. and Mrs. Chester M. McCloskey
- Dr. David J. Mathre
- Edith M. Roberts
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2015-10-01Created from EPrint's datestamp field
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2021-11-10Created from EPrint's last_modified field