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Conformational analysis of N,N,N-Trimethyl-(3,3-dimethylbutyl)ammonium iodide by NMR spectroscopy: a sterically hindered trans-standard

Liu, Albert Tianxiang and Nag, Mrinmoy and Carroll, William R. and Roberts, John D. (2013) Conformational analysis of N,N,N-Trimethyl-(3,3-dimethylbutyl)ammonium iodide by NMR spectroscopy: a sterically hindered trans-standard. Magnetic Resonance in Chemistry, 51 (11). pp. 701-704. ISSN 0749-1581. http://resolver.caltech.edu/CaltechAUTHORS:20131104-080637603

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Abstract

A predominantly trans-1,2-disubstituted ethane system – N,N,N-trimethyl-(3,3-dimethylbutyl)ammonium iodide – is of particular interest for conformational analysis, because it contains both an organic and a highly polar substituent, making it soluble and thus applicable to study in a large variety of solvents. The fraction of the trans conformer of this molecule in a wide range of protic and aprotic solvents was determined by the nuclear magnetic resonance proton couplings to be approximately 90%, in contrast to the previously assumed 100%. The consistently strong preference of the trans conformation should establish N,N,N-trimethyl-(3,3-dimethylbutyl)ammonium iodide as a possibly useful ‘trans-standard’ in conformational analysis, much more so than 1,2-ditert-butylethane, which has a poor solubility in many solvents.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/mrc.4003DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.4003/abstractPublisherArticle
Additional Information:© 2013 John Wiley & Sons, Ltd. Received: 15 May 2013; Revised: 1 August 2013; Accepted: 3 August 2013. Article first published online: 22 Sep. 2013. This research was supported by the National Science Foundation under grant CHE0543620, the Petroleum Research Fund of the American Chemical Society, the Senior Mentor Grant of the Camille and Henry Dreyfus Foundation, the McCloskey NORAC Fund, and the Summer Undergraduate Research Fellowship Program (SURF) at California Institute of Technology.
Funders:
Funding AgencyGrant Number
NSFCHE0543620
American Chemical Society Petroleum Research FundUNSPECIFIED
Camille and Henry Dreyfus Foundation Senior Mentor GrantUNSPECIFIED
McCloskey NORAC FundUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Subject Keywords:NMR; H-1; N; N; N-trimethyl-(3; 3-dimethylbutyl)ammonium iodide; conformational analysis; trans-standard
Record Number:CaltechAUTHORS:20131104-080637603
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20131104-080637603
Official Citation:Liu, A. T., Nag, M., Carroll, W. R. and Roberts, J. D. (2013), Conformational analysis of N,N,N-Trimethyl-(3,3-dimethylbutyl)ammonium iodide by NMR spectroscopy: a sterically hindered trans-standard. Magn. Reson. Chem., 51: 701–704. doi: 10.1002/mrc.4003
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:42206
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:04 Nov 2013 17:18
Last Modified:04 Nov 2013 17:18

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