Piro, Nicholas A. and Stein, Robin S. and Roberts, John D. (2004) Conformations of N,N-diethyl-β-alanine and β-alanine as a function of solvent. Journal of Physical Organic Chemistry, 17 (5). pp. 418-422. ISSN 0894-3230. doi:10.1002/poc.745. https://resolver.caltech.edu/CaltechAUTHORS:20151001-101402032
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Abstract
Conformational equilibria of N,N-diethyl-β-alanine were estimated from vicinal proton–proton coupling constants between the —CH_2—CH_2—group in protic and aprotic solvents of different polarities. β-Alanine was similarly studied in dimethyl sulfoxide (DMSO). In general, the results for both substances correspond fairly well with those reported earlier for β-alanine in neutral and acidic aqueous solutions. There appeared to be little conformational preference for N,N-diethyl-β-alanine in any of the solvents used, ranging from water to dichloromethane. The exception was a moderate preference (66–73%) for the trans conformer displayed by the conjugate base of N,N-diethyl-β-alanine in all of the solvents studied.
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| Additional Information: | © 2004 John Wiley & Sons, Ltd. Received 2 October 2003; revised 16 December 2003; accepted 19 December 2003. Acknowledgment is made to 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 E. I. Du Pont Company, Merck and Company, Dr & Mrs Chester M. McCloskey and the Camille and Henry Dreyfus Foundation for their helpful financial assistance. | ||||||||||||||
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| Subject Keywords: | N,N-diethyl-β-alanine; β-alanine; conformation; solvent | ||||||||||||||
| Issue or Number: | 5 | ||||||||||||||
| DOI: | 10.1002/poc.745 | ||||||||||||||
| Record Number: | CaltechAUTHORS:20151001-101402032 | ||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151001-101402032 | ||||||||||||||
| Official Citation: | Piro, N. A., Stein, R. S. and Roberts, J. D. (2004), Conformations of N,N-diethyl-β-alanine and β-alanine as a function of solvent. J. Phys. Org. Chem., 17: 418–422. doi: 10.1002/poc.745 | ||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
| ID Code: | 60649 | ||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||||||
| Deposited On: | 04 Nov 2015 16:27 | ||||||||||||||
| Last Modified: | 10 Nov 2021 22:37 |
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