Abstract
The pKa and \(pK_{BH^ + }\) values of a series of 3(5)-azido-1,2,4-triazoles are correlated with the σ I and σ C constants according to the equation pK =ρIσI + ρCσC + pKo. The high ρ I values in both cases are due to the closeness of the substituent to the reaction center. The ρ C/ρI ratio attests to different contributions of the inductive and mesomeric effects of a substituent during transmission of its effect from the 5-position to the N1 and N4 heteroatoms.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
C. F. Kröger and W. Freiberg, Z. Chem., 5, 381 (1965).
W. Freiberg and C. F. Kröger, Chimia, 21, 159 (1967).
L. I. Bagal and M. S. Pevzner, Khim. Geterotsikl. Soedin., 558 (1970).
S. Patai, The Chemistry of the Azido Group, New York (1972), Chap. 4.
K. Yates and R. A. McClelland, J. Amer. Chem. Soc., 89, 2686 (1967).
Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], RGU (1966), p. 85.
E. Berliner, J. Amer. Chem. Soc., 75, 2417 (1953).
L. I. Litvinenko, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1737 (1962).
M. Charton, J. Org. Chem., 30, 3346 (1965).
M. Charton, J. Amer. Chem. Soc., 91, 6649 (1969).
M. Charton, J. Amer. Chem. Soc., 86, 2033 (1964).
V. V. Mel'nikov, M. S. Pevzner, V. V. Stolpakova, and L. F. Khor'kova, Khim. Geterotsikl. Soedin., 409 (1971).
H. H. Takimoto, G. C. Denault, and S. Hotta, J. Org. Chem., 30, 711 (1965).
L. I. Bagal, M. S. Pevzner, V. Ya. Samarenko, and A. P. Egorov, Khim. Geterotsikl. Soedin., 997 (1970).
A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen (1962).
C. D. Johnson, A. R. Katritzky, and S. A. Shapiro, J. Amer. Chem. Soc., 91, 6654 (1969).
R. Stewart and M. R. Granger, Can. J. Chem., 39, 2508 (1961).
L. M. Batuner and M. E. Pozin, Mathematical Methods in Chemical Technique [in Russian], Khimiya, Leningrad (1971), p. 689.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1288–1291, September, 1974.
Rights and permissions
About this article
Cite this article
Pevzner, M.S., Martynova, M.N. & Timofeeva, T.N. Acid — Base properties of 3(5)-azido-1,2,4-triazoles. Chem Heterocycl Compd 10, 1121–1123 (1974). https://doi.org/10.1007/BF00472140
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00472140