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Conformational equilibria of ephedrine and pseudoephedrine and hydrogen bonding

โœ Scribed by Helen Tsai; John D. Roberts


Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
280 KB
Volume
30
Category
Article
ISSN
0749-1581

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โœฆ Synopsis


Abstract

Proton NMR spectra suggest that the conformation with trans vicinal hydrogens is favored for ephedrine as the free base in deuterium oxide, although in nonโ€polar solvents, such as deuteriotrichloromethane, the gauche vicinal hydrogen conformations are favored, as has been reported previously. The conjugate acid has primarily gauche hydrogens. In contrast, the transโ€hydrogen rotamers of pseudoephedrine dominate for both the nonโ€protonated and protonated forms in deuterium oxide. Hydrogen bonding is unlikely to be as important as usually assumed in determining the conformational preferences of these substances.


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