ISSN:
0749-1581
Keywords:
17O NMR
;
N-Arylacetamides
;
Arylacetates
;
Torsion angle
;
Electronic effects
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
17O NMR spectroscopic data at natural abundance in acetonitrile at 75°C were obtained for sixteen N-arylacetamides, three N-methyl-N-arylacetamides and seven aryl acetates. The 17O chemical shifts of the N-arylacetamides are significantly influenced by both electronic and steric factors. A Hammett plot of the data for 4-substituted N-arylacetamides gives a slope of 22 ppm. Ortho substituents result in significant shielding effects, in contrast to previously reported results for conjugated ketnoes. A quantitative relationship between 17O chemical shift data and torsion angle was found for the sterically hindered arylacetamides. Electronic effects on the aryl acetate 17O chemical shifts are, in comparison, greatly reduced. Steric factors for aryl acetates show even smaller effects on the 17O chemical shifts.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260260106
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