Abstract
The acid-base equilibrium behavior of alkyl(phenyl)-substituted 3-hydroxypyridines and 5-hydroxypyrimidines, and their dependence on pH values in aqueous solution, on the solvent, and on the phase composition, have been studied using UV spectroscopy. It has been found that in neutral aqueous solution all of the substituted 3-hydroxypyridines examined contain, in addition to the neutral form, a bipolar form, whose concentration depends on the nature and position of the substituent. In contrast, methyl substituted 5-hydroxypyrimidines form significant amounts of the bipolar form only in more acidic media.
Similar content being viewed by others
Literature Cited
L. D. Smirnov and K. M. Dyumaev, Khim.-farm. Zh., No. 4, 28 (1984).
W. Sirrenberg, F. Maurer, E. Klanke, B. Becher, and W. Stendel (Bayer A. G.), German Patent No. 3311703; C. A., 102, 78904 (1985).
D. E. Metzler, C. M. Harris, R. J. Johnson, D. B. Siano, and J. A. Thomson, Biochemistry, 12, 5377 (1973).
S. F. Mason, J. Chem. Soc., No. 12, 5010 (1957).
J. M. Sanchez-Ruiz, J. Llor, and M. Cortigo, J. Chem. Soc., Perkin Trans. 2, No. 12, 2047 (1984).
D. Heinert and A. E. Martell, J. Am. Chem. Soc., 81, 3933 (1959).
D. J. Brown, The Pyrimidines, Interscience, New York-London (1962).
V. P. Lezina, A. U. Stepanyants, N. I. Golovkina, and L. D. Smirnov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 98 (1980).
V. P. Lezina, M. M. Kozlova, S. B. Gashev, A. U. Stepanyants, and L. D. Smirnov, Khim. Geterotsikl. Soedin., No. 8, 1111 (1986).
N. Ya. Bernstein and Yu. L. Kaminskii, Spectrometric Analysis in Organic Chemistry [in Russian], Khimiya, Moscow (1975).
T. N. Rodionova, R. E. Lokhov, and K. M. Dyumaev, Khim. Geterotsikl. Soedin., No. 7, 962 (1972).
W. Gruber, Can. J. Chem., 31, 364 (1953).
J. H. Chesterfield, J. F. McOmie, and M. S. Tute, J. Chem. Soc., No. 11, 4590 (1960).
A. Dornow and H. Hell, Chem. Ber., 93, 1998 (1960).
S. B. Gashev, V. F. Sedova, L. D. Smirnov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 9, 1257 (1983).
H. Brederek, R. Gompper, and H. Herlinger, Chem. Ber., 91, 2832 (1958).
S. B. Gashev, B. A. Korolev, L. A. Osmolovskaya, and L. D. Smirnov, Khim. Geterotsikl. Soedin., No. 9, 1262 (1983).
Author information
Authors and Affiliations
Additional information
Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1099, August, 1989.
Rights and permissions
About this article
Cite this article
Korobeinicheva, I.K., Sedova, V.F., Gashev, S.B. et al. UV spectroscopic study of the acid-base reactions of 3-hydroxypyridines and 5-hydroxypyrimidines. Chem Heterocycl Compd 25, 913–919 (1989). https://doi.org/10.1007/BF00479612
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00479612