Published August 7, 2002
| Version Supplemental Material
Journal Article
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An NMR and Quantum Mechanical Investigation of Solvent Effects on Conformational Equilibria of Butanedinitrile
Creators
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1.
California Institute of Technology
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2.
DuPont (United States)
Abstract
Vicinal proton−proton NMR couplings and ab initio quantum mechanics have been used to investigate solvent effects on conformational equilibria of butanedinitrile. The trans and gauche conformations are about equally favored at room temperature in solvents of low dielectric constant while the equilibrium is essentially the statistical proportions of one-third trans and two-thirds gauche in water with a high dielectric constant. The coupling assignments were confirmed with the aid of stereospecific deuterium-labeled (R,R or S,S)-1,2-dideuteriobutanedinitrile. The calculations support the observed trends. Similar results were observed for 1,2-dibromo- and dichloroethanes.
Additional Information
© 2002 American Chemical Society. Received April 12, 2002. Publication Date (Web): July 10, 2002. We thank the donors of the Petroleum Research Fund, administered by the American Chemical Society, for support of this research. We are also deeply indebted to the Summer Undergraduate Research Fellowship Program (SURF), the Beckman Institute of the California Institute of Technology, the E. I. Du Pont Co., and Dr. & Mrs. Chester M. McCloskey for their helpful financial assistance. D.R.K. is grateful for support of part of this research by a graduate fellowship from the Fannie and John Hertz Foundation. The quantum chemistry calculations reported here were funded by DOE-BCTR (DEFG36-93CH105 81, David Boron). The facilities of the MSC are also supported by grants from NSF (CHE 95-22179 and ASC 92-100368), Chevron Petroleum Technology Co., Saudi Aramco, Asahi Chemical, Owens-Corning, Exxon, Chevron Chemical Co., Chevron Research and Technology Co., Avery-Dennison, Hercules, BP Chemical, and the Beckman Institute.Attached Files
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Additional details
Identifiers
- Eprint ID
- 60653
- Resolver ID
- CaltechAUTHORS:20151001-101403030
Related works
- Describes
- http://pubs.acs.org/doi/suppl/10.1021/ja020535n (URL)
Funding
- American Chemical Society Petroleum Research Fund
- Caltech Summer Undergraduate Research Fellowship (SURF)
- E. I. Du Pont Co.
- Dr. & Mrs. Chester M. McCloskey
- Fannie and John Hertz Foundation
- Department of Energy (DOE)
- DE-FG36-93CH10581
- NSF
- CHE 95-22179
- NSF
- ASC 92-100368
- Chevron Petroleum Technology Co.
- Chevron Research and Technology Co.
- Avery-Dennison
- Caltech Beckman Institute
- Hercules
- BP Chemical
Dates
- Created
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2015-10-02Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field