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Conformational Equilibria of N,N-Dimethylsuccinamic Acid and Its Lithium Salt as a Function of Solvent

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. http://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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http://dx.doi.org/10.1021/ol302573bDOIUNSPECIFIED
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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.
Funders:
Funding AgencyGrant Number
NSFCHE-0543620
NSFTG-CHE1000106
American Chemical Society Petroleum Research FundUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Camille and Henry Dreyfus Foundation Senior Scientist Mentor ProgramUNSPECIFIED
NORAC GrantUNSPECIFIED
Merck and CompanyUNSPECIFIED
DURIP-ONRUNSPECIFIED
DURIP-AROUNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
Army Research Office (ARO)UNSPECIFIED
NSFUNSPECIFIED
NIHUNSPECIFIED
Department of Energy (DOE)UNSPECIFIED
ChevronUNSPECIFIED
NissanUNSPECIFIED
Dow CorningUNSPECIFIED
IntelUNSPECIFIED
PfizerUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Sanofi-AventisUNSPECIFIED
Record Number:CaltechAUTHORS:20130404-133423655
Persistent URL:http://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:15 Apr 2013 19:20

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