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. doi:10.1021/ol030089o. https://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.

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Article

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URL	URL Type	Description
http://dx.doi.org/10.1021/ol030089o	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ol030089o	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ol030089o	Related Item	Supporting 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 Agency	Grant Number
American Chemical Society Petroleum Research Fund	UNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)	UNSPECIFIED
E. I. Du Pont Company	UNSPECIFIED
Dr. and Mrs. Chester M. McCloskey	UNSPECIFIED
Camille and Henry Dreyfus Foundation	UNSPECIFIED
Merck and Company	UNSPECIFIED

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DOI:

10.1021/ol030089o

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CaltechAUTHORS:20151001-101402532

Persistent URL:

https://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

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ID Code:

60651

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CaltechAUTHORS

Deposited By:

Ruth Sustaita

Deposited On:

02 Oct 2015 19:28

Last Modified:

10 Nov 2021 22:37

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