Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry
Publication
, Journal Article
Porter, NA; Ok, D; Huff, JB; Adams, CM; McPhail, AT; Kim, K
Published in: Journal of the American Chemical Society
March 1, 1988
Four two-chain dicarboxylic acid surfactants linked with a carbonyl group were synthesized and studied. The compounds exist as meso and (±) diastereomers, and they form aggregates, presumably micelles, at concentrations >10−5 M. Equilibration of the diacids in benzene at 60 °C (p-toluenesulfonic acid catalyst) gives a 50/50 mixture of meso and (±) diastereomers. Equilibration of the diacids in aqueous base with or without added cosurfactants (CTAB, DDAB) gives mixtures favoring the meso diastereomer by as much as 90/10. This perturbation of diastereomeric equilibria is discussed in terms of hydrophobic enforcement of organic stereochemistry. © 1988, American Chemical Society. All rights reserved.
Duke Scholars
Published In
Journal of the American Chemical Society
DOI
EISSN
1520-5126
ISSN
0002-7863
Publication Date
March 1, 1988
Volume
110
Issue
6
Start / End Page
1896 / 1901
Related Subject Headings
- General Chemistry
- 40 Engineering
- 34 Chemical sciences
- 03 Chemical Sciences
Citation
APA
Chicago
ICMJE
MLA
NLM
Porter, N. A., Ok, D., Huff, J. B., Adams, C. M., McPhail, A. T., & Kim, K. (1988). Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry. Journal of the American Chemical Society, 110(6), 1896–1901. https://doi.org/10.1021/ja00214a038
Porter, N. A., D. Ok, J. B. Huff, C. M. Adams, A. T. McPhail, and K. Kim. “Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry.” Journal of the American Chemical Society 110, no. 6 (March 1, 1988): 1896–1901. https://doi.org/10.1021/ja00214a038.
Porter NA, Ok D, Huff JB, Adams CM, McPhail AT, Kim K. Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry. Journal of the American Chemical Society. 1988 Mar 1;110(6):1896–901.
Porter, N. A., et al. “Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry.” Journal of the American Chemical Society, vol. 110, no. 6, Mar. 1988, pp. 1896–901. Scopus, doi:10.1021/ja00214a038.
Porter NA, Ok D, Huff JB, Adams CM, McPhail AT, Kim K. Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry. Journal of the American Chemical Society. 1988 Mar 1;110(6):1896–1901.
Published In
Journal of the American Chemical Society
DOI
EISSN
1520-5126
ISSN
0002-7863
Publication Date
March 1, 1988
Volume
110
Issue
6
Start / End Page
1896 / 1901
Related Subject Headings
- General Chemistry
- 40 Engineering
- 34 Chemical sciences
- 03 Chemical Sciences