Quantum-chemical study on the tautomerism of primary nitramines: the mechanism of N-nitro-anion protonation excludingaci-form formation |
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Authors: | V. G. Avakyan O. V. Fateyev |
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Affiliation: | (1) A.V.Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 117912 Moscow, Russian Federation |
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Abstract: | The values of the energy barriers to intramolecular 1,3-H shift reactions, in whichaci-forms of N- and C-nitro-compounds:1 and are capable of transforming into2 and, respectively, have been calculated by the semi-empirical AM1 method. The barrier heights (39 and 59.4 kcal/mol) reflect the kinetic stability of both tautomeric forms of the N- and C-nitro-compounds.Ab initio calculations in the 3–21G basis set of the structure and energies of stationary points on the potential energy surface of the system MeN=NO2 H3O demonstrated that there exists the principal possibility of the formation of only tautomer 2 (which is more stable than1).Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No 1, pp. 100–104, January, 1993. |
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Keywords: | tautomerism of C- and N-nitro-compounds primary nitramines aci-forms of primary nitramines cyclic H-bonded complexes. |
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