Rate Processes and Nuclear Magnetic Resonance Spectra. II. Hindered Internal Rotation of Amides

DOI PDF 被引用文献55件
  • H. S. Gutowsky
    Noyes Chemical Laboratory, University of Illinois, Urbana, Illinois
  • C. H. Holm
    Noyes Chemical Laboratory, University of Illinois, Urbana, Illinois

書誌事項

公開日
1956-12-01
DOI
  • 10.1063/1.1743184
公開者
AIP Publishing

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説明

<jats:p>Mathematical methods are presented for calculating rate constants of processes which narrow nuclear magnetic resonance absorption lines having discrete components. High resolution proton spectra show that the R1CO-NR2R3 skeletons of N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMA) are planar and suggest that N-methylformamide, N-methylacetamide, N-methylformanilide and N-methylacetanilide exist predominantly in one configuration. The presence of a significant amount of double bond character in the C–N amide bond is proved by the temperature dependent coalescence observed for the chemically shifted proton doublet of the N(CH3)2 groups in DMF and DMA, which gives values of about 22 and 19 kcal respectively for the free energy of activation required for reorientations about the bond.</jats:p>

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