Abstract
A relationship was established between the structure of amino-1-methylnitropyrazoles and the first stages of their fragmentation under electron impact, viz., the elimination of NO, NO2, and OH radicals. In contrast to other “ortho” isomers, 4-amino-1-methyl-3-nitropyrazole displays autonomous properties of amino and nitro aromatic compounds as a consequence of weakening of the interaction of the amino and nitro groups along the C(3)-C(4) bond and specific redistribution of the electron density in the pyrazole ring.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. N. Kost and I. I. Grandberg, Adv. Heterocycl. Chem., 6, 347 (1966).
S. D. Sokolov, Usp. Khim., No. 3, 533 (1979).
V. P. Perevalov, L. I. Baryshnenkova, M. A. Andreeva, Yu. A. Manaev, I. A. Denisova, B. I. Stepanov, and V. I. Seraya, Khim. Geterotsikl. Soedin., No. 12, 1672 (1983).
V. P. Perevalov, M. A. Andreeva, L. I. Baryshnenkova, Yu. A. Manaev, G. S. Yamburg, B. I. Stepanov, and V. A. Dubrovskaya, Khim. Geterotsikl. Soedin., No. 12, 1676 (1983).
S. A. Giller, I. B. Mazheika, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 1, 130 (1967).
I. I. Grandberg, S. V. Tabak, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 1, 85 (1966).
V. T. Sahini and C. Rodina, Rev. Roum. Chim., 18, 1283 (1973).
R. A. Khmel'nitskii and P. B. Terent'ev, Usp. Khim., 48, 854 (1979).
P. B. Terent'ev, Mass Spectrometry in Organic Chemistry [in Russian], Vyssh. Shkola, Moscow (1979), p. 223.
R. Silverstein, G. Bassler, and T. Morril, Spectrometric Identification of Organic Compounds, Wiley, New York (1974).
H. Feuer (ed.), The Chemistry of the Nitro and Nitroso Groups, Wiley-Interscience, New York (1969).
R. A. Khmel'nitskii, A. P. Krasnoshchek, A. A. Polyakova, and I. I. Grandberg, Zh. Org. Khim., 3, 1540 (1967).
M. A. Khan and B. M. Lynch, Can. J. Chem., 49., 3566 (1971).
A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Leningrad (1972), p. 198.
Yu. A. Manaev, M. A. Andreeva, V. P. Perevalov, B. I. Stepnov, V. A. Dubrovskaya, and V. I. Seraya, Zh. Obshch. Khim., 52, 2592 (1982).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 555–558, April, 1985.
Rights and permissions
About this article
Cite this article
Perevalov, V.P., Bezborodov, B.V., Baryshnenkova, L.I. et al. Mass-spectrometric investigation of amino-1-methylnitropyrazoles. Chem Heterocycl Compd 21, 465–468 (1985). https://doi.org/10.1007/BF00504415
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00504415