Abstract
Features of the change in the chemical shifts of the protons of substituted pyridine-, pyrimidine-, 3-hydroxypyridine-, and 5-hydroxypyrimidine-1-oxides, as dependent on the basicity of the medium, were investigated. The ionization constants and the possible forms of the occurrence of the molecules were determined. The character of the influence of the substituents (alkyl, hydroxyl) on the pKa values and the PMR spectral parameters was obtained. The comparison of the results obtained with the data on substituted pyridines and pyrimidines was carried out.
Similar content being viewed by others
Literature Cited
V. P. Lezina, M. M. Kozlova, S. B. Gashev, A. U. Stepanyants, and L. D. Smirnov, Khim. Geterotsikl. Soedin., No. 8, 1111 (1986).
A. Albert and J. N. Philips, J. Chem. Soc., No. 6, 1294 (1956).
H. H. Jaffe, J. Am. Chem. Soc., 77, 4445 (1955).
V. P. Lezina, A. U. Stepanyants, N. I. Golovkina, and L. D. Smirnov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 98 (1980).
S. B. Gashev, B. A. Korolev, L. A. Osmolovskaya, and L. D. Smirnov, Khim. Geterotsikl. Soedin., No. 9, 1262 (1983).
G. G. Dvoryantseva, M. M. Kaganskii, I. S. Musatova, and A. S. Elina, Khim. Geterotsikl. Soedin., No. 11, 1554 (1974).
T. N. Ul'yanova, G. G. Dvoryantseva, L. M. Alekseeva, Yu. N. Sheinker, and A. S. Elina, Khim. Geterotsikl. Soedin., No. 6, 846 (1971).
C. D. Johnson, A. R. Katritzky, and S. A. Shapiro, J. Am. Chem. Soc., 91, 6654 (1969).
Author information
Authors and Affiliations
Additional information
For Communication 1, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1369–1376, October, 1987.
Rights and permissions
About this article
Cite this article
Lezina, V.P., Kozlova, M.M., Gashev, S.B. et al. Acid-base conversions of nitrogen heterocycles by the method of NMR spectroscopy. 2. Substituted pyridine- and pyrimidine-1-oxides. Chem Heterocycl Compd 23, 1098–1105 (1987). https://doi.org/10.1007/BF00476541
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00476541