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Applications of 15 N NMR spectroscopy to the study of unsymmetrically N ‐substituted amides and model peptide compounds
Author(s) -
Dorie J.,
Gouesnard J. P.,
Mechin B.,
Naulet N.,
Martin G. J.
Publication year - 1980
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270130214
Subject(s) - diastereomer , steric effects , chemistry , formamides , alkyl , lone pair , chemical shift , spectroscopy , nuclear magnetic resonance spectroscopy , peptide , stereochemistry , computational chemistry , organic chemistry , molecule , biochemistry , physics , formamide , quantum mechanics
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.