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Conformations of 2-Carboxy-1,4-butanedioic Acid as a Function of Ionization State in Dimethyl Sulfoxide

Nair, Gautham and Roberts, John D. (2003) Conformations of 2-Carboxy-1,4-butanedioic Acid as a Function of Ionization State in Dimethyl Sulfoxide. Organic Letters, 5 (20). pp. 3699-3701. ISSN 1523-7060. http://resolver.caltech.edu/CaltechAUTHORS:20151001-101402532

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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.


Item Type:Article
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http://dx.doi.org/10.1021/ol030089oDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol030089oPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol030089oRelated ItemSupporting Information
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.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
E. I. Du Pont CompanyUNSPECIFIED
Dr. and Mrs. Chester M. McCloskeyUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck and CompanyUNSPECIFIED
Record Number:CaltechAUTHORS:20151001-101402532
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151001-101402532
Official Citation:Conformations of 2-Carboxy-1,4-butanedioic Acid as a Function of Ionization State in Dimethyl Sulfoxide Gautham Nair and and John D. Roberts* Organic Letters 2003 5 (20), 3699-3701 DOI: 10.1021/ol030089o
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60651
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:02 Oct 2015 19:28
Last Modified:02 Oct 2015 19:28

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