Abstract
It was shown by MNDO calculations that the stability of the 3,5-dimethyl-1H-pyrazole-4-diazonium ion to decomposition with the elimination of nitrogen is due to the destabilization of the formed carbocation, which has a triplet ground electronic state.
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R. P. Brint, D. J. Coverney, and F. L. Lalor, J. Chem. Soc. Perkin 2, No. 2, 139 (1985).
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).
M. A. Vincent and L. Radom, J. Am. Chem. Soc., 100, 3306 (1978).
V. I. Minkin, B. Ya. Simkin, and R. M. Minyaev, Quantum Chemistry of Organic Compounds. Reaction Mechanisms [in Russian], Khimiya, Moscow (1986), Chap. 2.
W. J. Hehre, R. Ditchfield, L. Radom, and J. A. Pople, J. Am. Chem. Soc., 92, 4796 (1970).
J. D. Dill, P. R. Schleyer, J. S. Binkley, R. Seeger, J. A. Pople, and E. Haselbach, J. Am. Chem. Soc., 98, 5428 (1976).
A. T. Pilipenko, V. A. Zaets, V. D. Khavryuchenko, and E. R. Falendysh, Zh. Strukt. Khim., 28, No. 5, 155 (1987).
Quantum Chemistry Program Exchange, Program N506 (AMPAC).
M. J. S. Dewar and S. Olivella, J. Chem. Soc., Faraday, 75, 829 (1979).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 349–351, March, 1990.
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Glukhovtsev, M.N., Yudilevich, I.A. & Simkin, B.Y. Quantum-chemical investigation of the factors which determine stability of the 3,5-dimethyl-1H-pyrazole-4-diazonium ion. Chem Heterocycl Compd 26, 298–300 (1990). https://doi.org/10.1007/BF00472549
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DOI: https://doi.org/10.1007/BF00472549