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Conformational Equilibria of Ethanolamine and Its Hydrochloride in Solution

Smith, Tim D. and Gerken, James B. and Jog, Parag V. and Roberts, John D. (2007) Conformational Equilibria of Ethanolamine and Its Hydrochloride in Solution. Organic Letters, 9 (22). pp. 4555-4557. ISSN 1523-7060. http://resolver.caltech.edu/CaltechAUTHORS:20150930-125951004

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Abstract

The conformational preferences of ethanolamine and its hydrochloride in solution were estimated by comparing experimental NMR vicinal proton−proton coupling constants to semiemprical coupling constants for each staggered rotamer, derived by the Haasnoot−Altona method. Strong gauche preferences are observed for both ethanolamine and its hydrochloride over a wide range of solvent polarities. Concentration was not observed to significantly affect the position of the conformer equilibria.


Item Type:Article
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http://dx.doi.org/10.1021/o17020077DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol7020077PublisherArticle
Additional Information:© 2007 American Chemical Society. Received August 16, 2007. Publication Date (Web): October 2, 2007. Acknowledgment is made to the donors of the Petroleum Research Fund administered by the American Chemical Society for their support of this research. This material is also based upon work supported by the National Science Foundation under Grant No. CHE-0543620, the Summer Undergraduate Research Fellowship Program (SURF) at the California Institute of Technology as supported by the Howard Hughes Medical Institute, and the Senior Scientist Mentor Program of the Camille and Henry Dreyfus Foundation. In addition, we are indebted to Merck & Company, Dr. & Mrs. Chester M. McCloskey, Dr. David J. Mathre, and Edith M. Roberts for their helpful financial assistance. The authors thank Taylor Lenton for her generous assistance with the laboratory work at Caltech.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
NSFCHE-0543620
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck & CompanyUNSPECIFIED
Dr. and Mrs. Chester M. McCloskeyUNSPECIFIED
Dr. David J. MathreUNSPECIFIED
Edith M. RobertsUNSPECIFIED
Record Number:CaltechAUTHORS:20150930-125951004
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150930-125951004
Official Citation:Conformational Equilibria of Ethanolamine and Its Hydrochloride in Solution Tim D. Smith, James B. Gerken, Parag V. Jog, and John D. Roberts Organic Letters 2007 9 (22), 4555-4557 DOI: 10.1021/ol7020077
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60609
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:01 Oct 2015 17:14
Last Modified:01 Oct 2015 17:14

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