Abstract
The influence of the solvent on the [NH b] ⇌ [NH f] conformational equilibrium for the t-butyl esters of 3,3-diphenyl-3- benzoylaminopropionic acid and its 2-methyl and 2,2-dimethyl-substituted analogues was investigated. The calculated Δ G B.F S values of the free-energy difference of the corresponding conformers were correlated with ϕ(ϵ S) = (ϵ S−1)/ (2ϵ S + 1) parameters, which characterize the polarity of the medium. The present results confirm our previous conclusion about the increased conformational preference in the case of the esters of 2,3-substituted 3-benzoylaminopropionic acids due to the steric interaction between the α- and β-substituents. This effect stabilizes the NH⋯O=C (ester) intramolecular hydrogen bonding which is typical of these compounds. The method of Klaeboe for IR spectral determination of conformational equilibria in solution is extended to provide better statistical confidence in the results.
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