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- Title
Energy barriers to gas-phase unimolecular decomposition of mono- and dinitrotoluenes.
- Authors
Khrapkovskii, G.; Nikolaeva, E.; Egorov, D.; Chachkov, D.; Shamov, A.
- Abstract
Alternative paths of gas-phase unimolecular decomposition of three nitrotoluenes and six dinitrotoluenes, in particular homolytic dissociation of the C-N bond, nitro-nitrite rearrangement, intramolecular hydrogen transfer from the methyl to nitro group with formation of isomeric aci-nitrotoluenes, and various paths involving formation of bicyclic intermediates, have been studied at the DFT B3LYP/6-31+G(2 df, p) level of theory using GAUSSIAN 09 software package. The most energetically favorable path for o-nitrotoluene and 2,3-, 2,4-, 2,5-, and 2,6-dinitrotoluenes is the formation of aci-nitrotoluenes. The effect of the substrate structure on the competition between different mechanisms of these reactions has been analyzed.
- Subjects
UNIMOLECULAR decomposition; NITROTOLUENE; DINITROTOLUENES; NITRITES; HYDROGEN
- Publication
Russian Journal of Organic Chemistry, 2016, Vol 52, Issue 6, p791
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428016060063