Abstract
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.
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