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Conformational changes of butanedioic acid as a function of pH as determined from changes in vicinal proton-proton NMR couplings

Lit, Eugene S. and Mallon, Frederick K. and Tsai, Helen and Roberts, John D. (1993) Conformational changes of butanedioic acid as a function of pH as determined from changes in vicinal proton-proton NMR couplings. Journal of the American Chemical Society, 115 (21). pp. 9563-9567. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151002-123936012

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Abstract

Vicinal proton-proton NMR couplings have been used to estimate the changes in conformational equilibria for butanedioic acid in the progression of its diprotic to monoprotic to di-ionized forms as a function of pH, concentration, and nature of the counterion. The results support earlier conclusions that the K_1/K_2 ratio for butanedioic acid is little, if at all, affected by internal hydrogen bonding in the monoanion. Perhaps surprisingly, the conformational preferences are weak, despite the possibility of steric hindrance and strong stabilizations by hydrogen-bonding, induction, and/or electrostatic effects.


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http://dx.doi.org/10.1021/ja00074a022DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00074a022PublisherArticle
Additional Information:© 1993 American Chemical Society. Received September 1, 1992. Publication Date: October 1993. This research was supported by the Caltech Consortium in Chemistry and Chemical Engineering; founding members: E. I. du Pont de Nemours and Company, Inc., Eastman Kodak Company, and Minnesota Mining and Manufacturing Company. Additional support was provided by the Caltech Summer Undergraduate Research Program (SURF). We are indebted to Dominic McGrath and David Wheeler for their assistance during the initial phases of the investigation, to Dr. Jane Raymond for her help throughout, and very much to Professor Julius Rebek, Jr., of the Massachusetts Institute of Technology for a number of incisive suggestions regarding possible interpretations of the results.
Funders:
Funding AgencyGrant Number
E. I. du Pont de Nemours and CompanyUNSPECIFIED
Eastman Kodak CompanyUNSPECIFIED
Minnesota Mining and Manufacturing CompanyUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Record Number:CaltechAUTHORS:20151002-123936012
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151002-123936012
Official Citation:Conformational changes of butanedioic acid as a function of pH as determined from changes in vicinal proton-proton NMR couplings Eugene S. Lit, Frederick K. Mallon, Helen Y. Tsai, and John D. Roberts Journal of the American Chemical Society 1993 115 (21), 9563-9567 DOI: 10.1021/ja00074a022
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60713
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:02 Oct 2015 22:45
Last Modified:02 Oct 2015 22:45

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