Liu, Albert Tianxiang and Emenike, Bright U. and Carroll, William R. and Roberts, John D. (2013) Conformational Equilibria of N,N-Dimethylsuccinamic Acid and Its Lithium Salt as a Function of Solvent. Organic Letters, 15 (4). pp. 760-763. ISSN 1523-7060. doi:10.1021/ol302573b. https://resolver.caltech.edu/CaltechAUTHORS:20130404-133423655
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Abstract
The conformational preferences of N,N-dimethylsuccinamic acid and its Li^+ salt were estimated by comparing the respective experimental NMR vicinal proton–proton coupling constants to semiempirical coupling constants for each staggered conformer as derived by the Haasnoot–De Leeuw–Altona method. The strong gauche preferences for the Li^+ salts clearly depended more on the solvents’ hydrogen-bond donating strength (α) than on their hydrogen-bond accepting (β) counterpart, where α and β are the corresponding Kamlet–Taft parameters.
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| Additional Information: | © 2013 American Chemical Society. Received December 6, 2012; Publication Date (Web): January 30, 2013. We thank the National Science Foundation under Grants CHE-0543620, TG-CHE1000106 and the donors of the Petroleum Research Fund administered by the American Chemical Society for support for this research. Other important support came from the Summer Undergraduate Research Fellowship Program (SURF) at the California Institute of Technology, the Senior Scientist Mentor Program of the Camille and Henry Dreyfus Foundation, and the NORAC grant of Dr. and Mrs. Chester M. McCloskey. We are indebted to Merck and Company, Dr. David J. Mathre, and Edith M. Roberts for their helpful financial assistance. The facilities of the MCS used in these studies were established with grants from DURIP-ONR and DURIP-ARO, with additional support from ONR, ARO, NSF, NIH, DOE, Chevron, Nissan, Dow Corning, Intel, Pfizer, Boehringer- Ingelheim, and Sanofi-Aventis. | ||||||||||||||||||||||||||||||||||||||||||||
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| Issue or Number: | 4 | ||||||||||||||||||||||||||||||||||||||||||||
| DOI: | 10.1021/ol302573b | ||||||||||||||||||||||||||||||||||||||||||||
| Record Number: | CaltechAUTHORS:20130404-133423655 | ||||||||||||||||||||||||||||||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130404-133423655 | ||||||||||||||||||||||||||||||||||||||||||||
| Official Citation: | Conformational Equilibria of N,N-Dimethylsuccinamic Acid and Its Lithium Salt as a Function of Solvent Albert Tianxiang Liu, Bright U. Emenike, William R. Carroll, and John D. Roberts Organic Letters 2013 15 (4), 760-763 | ||||||||||||||||||||||||||||||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||||||||||||||||||||||||||||||
| ID Code: | 37767 | ||||||||||||||||||||||||||||||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||||||||||||||||||||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||||||||||||||||||||||||||||||||||
| Deposited On: | 15 Apr 2013 19:20 | ||||||||||||||||||||||||||||||||||||||||||||
| Last Modified: | 09 Nov 2021 23:31 |
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