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17O NMR studies on substituted N-arylacetamides and aryl acetates: Torsion angle and electronic effects

✍ Scribed by David W. Boykin; Gina H. Deadwyler; A. L. Baumstark

Publisher: John Wiley and Sons
Year: 1988
Tongue: English
Weight: 437 KB
Volume: 26
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260260106

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✦ Synopsis

0 NMR spectroscopic data at natural abundance in acetonitrile at 75OC were obtained for sixteen Narylacetamides, three N-methyl-N-arylacetamides and seven aryl acetates. The I7O chemical shifts of the Narylacetamides are significantly influenced by both electronic and steric factors. A Hammett plot of the data for kubstituted N-arylacetamides gives a slope of 22 ppm. Ortho substituents result in significant shielding effects, in contrast to previously reported results for conjugated ketones. A quantitative relationship between I7O chemical shift data and torsion angle was found for the sterically hindered arylacetamides. Electronic effects on the aryl acetate '"0 chemical shifts are, in comparison, greatly reduced. Steric factors for aryl acetates show even smaller effects on the '"0 chemical shifts. KEY WORDS "0 NMR N-Arylacetamides Aryl acetates Torsion angle Electronic effects

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