Hindered rotation in N-methylformamide. A peptide-bond model system

Hindered rotation in N-methylformamide. A peptide-bond model system

Barriers to rotation about the C-N bond in the cis and trans isomers of N-methylformamide have been determined by n.m.r. spectroscopy. Representative values are 20.7 and 22.0 kcal/mole. Arrhenius parameters have also been determined. These results are compared with C-N barriers for N,N-dimethylforma...

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Veröffentlicht in:Biochemical and biophysical research communications 1971-09, Vol.44 (5), p.1156-1161
Hauptverfasser: Neuman, Robert C., Jonas, Violet, Anderson, Karen, Barry, Ronald
Format: Artikel
Sprache:eng
Schlagworte:
Amides
Chemical Phenomena
Chemistry, Physical
Deuterium
Formamides
Formates
Magnetic Resonance Spectroscopy
Methylation
Models, Chemical
Peptides
Stereoisomerism
Thermodynamics
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Zusammenfassung:Barriers to rotation about the C-N bond in the cis and trans isomers of N-methylformamide have been determined by n.m.r. spectroscopy. Representative values are 20.7 and 22.0 kcal/mole. Arrhenius parameters have also been determined. These results are compared with C-N barriers for N,N-dimethylformamide and unsubstituted formamide. The data suggest that C-N rotational barriers for N-methyl amides may be similar to those for their N,N-dimethyl derivatives.
ISSN:0006-291X
1090-2104
DOI:10.1016/S0006-291X(71)80207-3