Conformational analysis of N,N,N-Trimethyl-(3,3-dimethylbutyl)ammonium iodide by NMR spectroscopy: a sterically hindered trans-standard
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.
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.Additional details
- Eprint ID
- 42206
- Resolver ID
- CaltechAUTHORS:20131104-080637603
- CHE0543620
- NSF
- American Chemical Society Petroleum Research Fund
- Camille and Henry Dreyfus Foundation Senior Mentor Grant
- McCloskey NORAC Fund
- Caltech Summer Undergraduate Research Fellowship (SURF)
- Created
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2013-11-04Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field