Stoichiometry, Association Constant, and Solvation Model of Chiral Hydroxyfuranones in the Presence of Pirkle's Alcohols

Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives

“…Pure enantiomers of 2,2,2-trifluoro-1-(9-anthryl)ethanol (1a, Figure 1), are mainly used as chiral solvating agents [1,2] and chiral selectors [1][2][3][4] due to their particular hydroxyl (OH) and methine (CH) acidity [5][6][7][8]. The calculated gas phase acidities for 1a, 1-(9-anthryl)ethanol (2a) and 2,2,2-trifluoroethanol have shown that the influence of 9-anthryl ring is more significant than the trifluoromethyl group in modifying the CH rather than the OH acidity of 1a; the trifluoromethyl group increases 6.0 kcal mol −1 the OH acidity more than the CH acidity, while the 9-anthryl group increases 17.0 kcal mol −1 the CH acidity more than the OH acidity [6].…”