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1H and 13C NMR spectra of the rotational isomers of N-hydroxymethylamides and derivatives

✍ Scribed by E. N. Gate; D. L. Hooper; M. F. G. Stevens; M. D. Threadgill; K. Vaughan

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
563 KB
Volume
23
Category
Article
ISSN
0749-1581

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✦ Synopsis

A series of N-hydroxymethylamides, RCONR'CH,OH, and their 0-methyl and 0-acetyl derivatives, have been studied by -C and 'H magnetic resonance spectroscopy. Signals have been assigned to the E and %isomers on the bask of the analysis of the fully coupled spectra, and by comparison of the chemical shifts with those of model compounds. The introduction of the hydroxy, alkoxy or acetoxy groups at the or-position of the N-akyl moiety causes a significant shift in the equilibrium towards the Erotamer compared with the unsubstituted N-akylamide. The predominant effect in determining the E : Z ratio appears to be the steric interaction between the carbonyl oxygen and the a-oxygen in the akyl moiety; intramolecular hydrogen bonding does not play a significant role in determining the rotamer populations of these molecules.

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