Conclusions
-
1.
Study has been made of the kinetics of thermal decomposition of pyrrole nitro derivatives with activation energies in the 35–57 kcal/mole range. It is suggested that the decomposition of 2-nitro and 2,5-dinitropyrroles follows a molecular mechanism, and the decomposition of nitropyrroles substituted at the heterocycle nitrogen atom a radical mechanism. The thermal stability of the pyrrole nitro derivatives increases on carrying the nitro group from theα to theβ position, and rises when the NH group hydrogen is replaced by a methyl group.
-
2.
Study of the kinetics of thermal breakdown has shown the stability of the salts of mononitro derivatives pyrrole, pyrazole, and imidazole in the solid state to fall off as the acidity of the nitroazole rises. Activation energies have been determined for the thermal breakdown of the salts of mononitro derivatives of five-membered nitrogen-containing heterocycles.
Similar content being viewed by others
Literature cited
K. Morgan and D. Morrey, Tetrahedron,22, 57 (1966).
E. N. Safonova, V. M. Belikov, and S. S. Novikov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk,1959,1130, 1307.
I. J. Rinkes, Rec. Trav. Chim.,53, 1167 (1934).
T. L. Cottrell, T. E. Gracham, and T. J. Reid, Trans. Faraday Soc.,47, 1089 (1951).
V. V. Dubikhin, G. M. Nazin, D. N. Sokolov, and G. B. Manelis, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1416.
T. L. Cottrell, Strengths of Chemical Bonds, 2nd ed., Butterworth (1958).
Concise Handbook of Physicochemical Constants [in Russian], Khimiya, Leningrad (1974), p. 116.
M. W. Austin, I. R. Blackborow, I. H. Ridd, and B. V. Smith, J. Chem. Soc.,1965, 1051.
G. Gallo, C. Pasquelucci, P. Radaelli, and G. Lanciny, J. Org. Chem.,29, 362 (1964).
Yu. Ya. Maksimov, Zh. Fiz. Khim.,45, 793 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2711–2716, December, 1977.
Rights and permissions
About this article
Cite this article
Sharnin, G.P., Khabirov, R.A., Nurgatin, V.V. et al. Thermal decomposition of nitro derivatives of nitrogen-containing five-membered heterocycles, in the gaseous phase and in solid aggregates. Russ Chem Bull 26, 2506–2510 (1977). https://doi.org/10.1007/BF00924553
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00924553