Conclusions
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1.
Based on kinetic regularities of the H/D exchange of hydrogen in 5-hydroxynicotinic, 5-hydroxypicolinic, and 3-hydroxyisonicotinic acids at 160° in the region pD > 5.0 it has been found that the reaction follows an electrophilic mechanism and that the α position of the ring, vicinal to the OH group, is the most reactive.
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2.
The proton exchange rate constants have been determined which characterize the contribution of the anionic form of theβ-hydroxypyridinecarboxylic acids to the H/D exchange reaction.
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V. P. Lezina, A. U. Stepanyants, L. D. Smirnov, and M. I. Vinnik, Izv. Akad. Nauk SSSR, Ser. Khim., 317 (1978).
P. Bellingham, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., 1226 (1967).
V. P. Lezina, L. V. Shirokova, M. M. Borunov, A. U. Stepanyants, and L. D. Smirnov, Izv. Akad. Nauk SSSR, Ser. Khim., 753 (1981).
P. K. Glasoc and F. A. Long, J. Phys. Chem., 188 (1960).
V. P. Lezina, A. U. Stepanyants, N. I. Golovkina, and L. D. Smirnov, Izv. Akad, Nauk SSSR, Ser. Khim., 98 (1980).
L. D. Smirnov, L. G. Stolyarova, V. P. Lezina, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 615 (1976).
L. D. Smirnov, L. G. Stolyarova, V. S. Zhuravlev, V. P. Lezina, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1658 (1976).
L. D. Smirnov, L. Sh. Stolyarova, L. V. Shirokova, and V. P. Lezina, Izv. Akad. Nauk SSSR, Ser. Khim., 452 (1977).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2218–2222, October, 1981.
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Lezina, V.P., Shirokova, L.V., Stolyarova, L.G. et al. PMR study of the kinetics of H/D exchange of β-hydroxypyridinecarboxylic acids. Russ Chem Bull 30, 1818–1821 (1981). https://doi.org/10.1007/BF00963399
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DOI: https://doi.org/10.1007/BF00963399