Solved: Evidence for restricted rotation around amide CO]N bonds comes from NMR studies

Chapter 26, Problem 26.52

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Evidence for restricted rotation around amide CO]N bonds comes from NMR studies. At room temperature, the 1H NMR spectrum of N,N-dimethylformamide shows three peaks: 2.9 d (singlet, 3 H), 3.0 d (singlet, 3 H), 8.0 d (singlet, 1 H). As the temperature is raised, however, the two singlets at 2.9 d and 3.0 d slowly merge. At 180 C, the 1H NMR spectrum shows only two peaks: 2.95 d (singlet, 6 H) and 8.0 d (singlet, 1 H). Explain this temperature-dependent behavior. N,N-Dimethylformamide H O

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