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Applications of 15N NMR spectroscopy to the study of unsymmetrically N-substituted amides and model peptide compounds

✍ Scribed by J. Dorie; J. P. Gouesnard; B. Mechin; N. Naulet; G. J. Martin

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
569 KB
Volume
13
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^13^C and ^15^N spectra of unsymmetrically N‐substituted formamides and alkyl‐, substituted alkyl‐, and arylcarboxamides, which can be considered as model peptide compounds, were determined and discussed in terms of nitrogen lone pair delocalization. Differential solvent shifts and through‐space steric effects are considered as a tentative explanation of the difference in screening between geometrical diastereoisomers. Z‐E assignment and the thermodynamic stability of diastereoisomers can also be predicted in some circumstances from a consideration of the ^15^N chemical shifts. Data concerning small peptides are discussed in the light of the results obtained using the model compounds.

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