Solvent Effect on the Isomeric Equilibrium of Carbohydrates: The Superior Ability of 2,2,2-Trifluoroethanol for Intramolecular Hydrogen Bond Stabilization

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• 作者：Antonio Molinaro ; Cristina De Castro ; Rosa Lanzetta ; Emiliano Manzo ; and Michelangelo Parrilli
• 刊名：Journal of the American Chemical Society
• 出版年：2001
• 出版时间：December 19, 2001
• 年：2001
• 卷：123
• 期：50
• 页码：12605 - 12610
• 全文大小：72K
• 年卷期：v.123,no.50(December 19, 2001)
• ISSN：1520-5126

文摘

The higher aptitude of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization incarbohydrates is suggested. This belief, arising from the analysis by ¹H NMR spectroscopy of the solventeffect of D₂O, DMSO-d₆, and 2,2,2-trifluoroethanol-d₃ on the isomeric equilibrium of caryophyllose, was alsoconfirmed by shifting of the conformational equilibria of -ribopyranose and of its methyl glycoside.