Abstract
Conformation and Rotation Barriers of Substituted Glyoxylic Acid Amides Semiempirical calculations predict an orthogonal orientation of the carbonyl groups in tertiary glyoxylic acid amides, which is in good agreement with an X-ray structure analysis of 5. Due to the influence of the α-carbonyl group, the rotation barrier in the substituted glyoxylic acid amides 2a–d, 3a, 3b, and 4–6 (ΔG#c = 84–92 kJ mol−1) is about 10 kJ/mol higher than in simple acid amides, as was found by dynamic NMR line shape analysis.
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