The condensation of (S)-2-amino-2-phenylethanol or (S)-2-amino-3- phenylpropanol with substituted benzaldehydes in methanol or water led to crystalline products, which proved to exist in CDCl 3 at 300 K as three-component (ring cis-open-ring trans) tautomeric mixtures. The electronic effects of the 2-aryl substituents on the tautomeric equilibria were described by the Hammett equation. Good correlations were found between the equilibrium constants and the Hammett-Brown parameter (σ +) of the substituent X on the 2-phenyl group.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry