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Conformational Preferences of N,N-Dimethylsuccinamate as a Function of Alkali and Alkaline Earth Metal Salts: Experimental Studies in DMSO and Water As Determined by ^1H NMR Spectroscopy

Lai, Holden W. H. and Liu, Albert Tianxiang and Emenike, Bright U. and Carroll, William R. and Roberts, John D. (2014) Conformational Preferences of N,N-Dimethylsuccinamate as a Function of Alkali and Alkaline Earth Metal Salts: Experimental Studies in DMSO and Water As Determined by ^1H NMR Spectroscopy. Journal of Physical Chemistry A, 118 (11). pp. 1965-1970. ISSN 1089-5639. PMCID PMC3983401. http://resolver.caltech.edu/CaltechAUTHORS:20140428-154312619

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Abstract

The fraction of gauche conformers of N,N-dimethylsuccinamic acid (1) and its Li^+, Na^+, K^+, Mg^(2+), Ca^(2+), and N(Bu)_4^+ salts were estimated in DMSO and D_2O solution by comparing the experimental vicinal proton−proton couplings determined by ^1H NMR spectroscopy with those calculated using the Haasnoot, de Leeuw, and Altona (HLA) equation. In DMSO, the gauche preferences were found to increase with decreasing Ahrens ionic radius of the metal counterion. The same trend was not seen in D_2O, where the gauche fraction for all of the metallic salts were estimated to be approximately statistical or less. This highlights the importance of metal chelation on the conformation of organic molecules in polar aprotic media, which has implications for protein folding.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jp4106508DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jp4106508PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jp4106508PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3983401/PubMed CentralArticle
Additional Information:© 2014 American Chemical Society. ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Published In Issue March 20, 2014; Article ASAP March 10, 2014; Just Accepted Manuscript February 07, 2014; Received: October 28, 2013; Revised: February 04, 2014. The authors declare no competing financial interest. Acknowledgement is made to the National Science Foundation under Grant CHE-0543620, TG-CHE1000106, and to 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 Amgen Foundation, the Senior Scientist Mentor Program of the Camille and Henry Dreyfus Foundation, and the Chemistry NORAC grant of Dr. and Mrs. Chester M. McCloskey. We are also indebted to Merck and Company, Dr. David J. Mathre, and Edith M. Roberts for their helpful financial assistance. The facilitates 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, DOW, 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
Amgen FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Dr. and Mrs. Chester M. McCloskey Chemistry NORAC GrantUNSPECIFIED
Merck and CompanyUNSPECIFIED
Dr. David J. MathreUNSPECIFIED
Edith M. RobertsUNSPECIFIED
Subject Keywords:physical organic chemistry
PubMed Central ID:PMC3983401
Record Number:CaltechAUTHORS:20140428-154312619
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20140428-154312619
Official Citation:Lai, H. W. H., Liu, A. T., Emenike, B. U., Carroll, W. R., & Roberts, J. D. (2014). Conformational Preferences of N,N-Dimethylsuccinamate as a Function of Alkali and Alkaline Earth Metal Salts: Experimental Studies in DMSO and Water As Determined by 1H NMR Spectroscopy. The Journal of Physical Chemistry A, 118(11), 1965-1970. doi: 10.1021/jp4106508
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:45256
Collection:CaltechAUTHORS
Deposited By: Aucoeur Ngo
Deposited On:28 Apr 2014 23:25
Last Modified:21 Jul 2017 18:26

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