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Communication | Regular issue | Vol 16, No. 3, 1981, pp.343-346
Published online, 1st January, 1970
DOI: 10.3987/R-1981-03-0343
Nuclear Magnetic Resonance Spectra of Heterocyclic Systems: The 15N Parameters of a Substituted Pyridone

C. A. Kingsbury,* M. D. Cliffton, S. Rajan, D. L. Durham, and J. H. Looker

*Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebrasa 68588, U.S.A.

Abstract

The 15N coupling constants to 13C and to 1H are reported for 2-hydroxymethyl-5-methoxy-1-phenyl-4-pyridone (1). The one-bond 15N-13C coupling constants are consistent with sp2 hybridized nitrogen. The 13C chemical shifts do not change much on protonation, but the 15N chemical shift undergoes a large change. The nmr data are discussed with regard to the question of the aromaticity of 4-pyridones. An improved synthesis of 1 is reported.