Abstract
The protonation of isomeric 1H-, 2H-, and 5H-tetrazolylacetic acids, as well as a series of 5-aryl-1H- and 5-aryl-2H-tetrazolylacetic acids, in aqueous sulfuric acid solutions was studied by IR, UV, and PMR spectroscopy. It is shown that all of the investigated tetrazolylacetic acids are protonated in the tetrazole ring at sulfuric acid concentrations up to 96%; the proton adds to the nitrogen atom in the 4 position.
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Literature cited
L. N. Agarkova, V. A. Ostrovskii, G. I. Koldobskii, and G. B. Erusalimskii, Zh. Org. Khim., 18, 1043 (1982).
G. I. Koldobskii, V. A. Ostrovskii, and V. S. Poplavskii, Khim. Geterotsikl. Soedin., No. 10, 1299 (1981).
V. S. Poplavskii, V. A. Ostrovskii, G. I. Koldobskii, and E. A. Kulikova, Khim. Geterotsikl. Soedin., No. 2, 264 (1982).
G. I. Koldobskii, V. A. Ostrovskii, and B. V. Gidaspov, Khim. Geterotsikl. Soedin., No. 7, 867 (1980).
E. M. Arnett, in: Modern Problems in Physical Organic Chemistry [Russian translation], Mir, Moscow (1967), p. 195.
Yu. L. Khaldna, Doctoral Dissertation, Tartu (1974).
R. Stewart and M. R. Granger, Can. J. Chem., 39, 2508 (1961).
Yu. L. Khaldna, Usp. Khim., 49, 1174 (1980).
N. C. Marziano, G. M. Cimino, and R. C. Passerini, J. Chem. Soc., Perkin II, No. 14, 1915 (1973).
R. A. Cox and K. Yates, J. Am. Chem. Soc., 100, 3861 (1978).
A. V. Moskvin, V. A. Ostrovskii, I. Yu. Shirobokov, G. I. Koldobskii, and B. V. Gidaspov, Zh. Org. Khim., 14, 2440 (1978).
F. Einberg, J. Org. Chem., 35, 3979 (1970).
C. R. Jacobson and E. D. Amstutz, J. Org. Chem., 21, 311 (1956).
R. T. Buckler, S. Hayo, O. J. Lorenzetti, L. F. Sancilio, H. E. Hartzler, and W. G. Strycker, J. Med. Chem., 13, 725 (1970).
M. I. Vinnik, Usp. Khim., 35, 1922 (1966).
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See [1] for communication 12.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1421–1425, October, 1982.
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Poplavskii, V.S., Ostrovskii, V.A. & Koldobskii, G.I. Tetrazoles. 13. Protonation of tetrazolylacetic acids. Chem Heterocycl Compd 18, 1107–1111 (1982). https://doi.org/10.1007/BF00503206
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DOI: https://doi.org/10.1007/BF00503206