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Solution conformational preferences of glutaric, 3-hydroxyglutaric, 3-methylglutaric acid, and their mono- and dianions

Gerken, James B. and Badger, Claire and Bisbee, Christopher and Gardner, Sasha and Qi, Yang and Vilà, Víctor Durà and Roberts, John D. (2008) Solution conformational preferences of glutaric, 3-hydroxyglutaric, 3-methylglutaric acid, and their mono- and dianions. Journal of Physical Organic Chemistry, 21 (3). pp. 193-197. ISSN 0894-3230 . http://resolver.caltech.edu/CaltechAUTHORS:20150930-125950470

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/poc.1277DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/poc.1277/abstractPublisherArticle
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.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
NSFCHE-0543620
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck & CompanyUNSPECIFIED
Dr. and Mrs. Chester M. McCloskeyUNSPECIFIED
Dr. David J. MathreUNSPECIFIED
Edith M. RobertsUNSPECIFIED
Subject Keywords:conformation; NMR; glutaric acids
Record Number:CaltechAUTHORS:20150930-125950470
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150930-125950470
Official Citation:Gerken, J. B., Badger, C., Bisbee, C., Gardner, S., Qi, Y., Vilà, V. D. and Roberts, J. D. (2008), Solution conformational preferences of glutaric, 3-hydroxyglutaric, 3-methylglutaric acid, and their mono- and dianions. J. Phys. Org. Chem., 21: 193–197. doi: 10.1002/poc.1277
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60608
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:01 Oct 2015 17:41
Last Modified:01 Oct 2015 17:41

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