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THE INFLUENCE OF LEWIS ACID CATALYST ON THE KINETIC AND MOLECULAR MECHANISM OF NITROUS ACID ELIMINATION FROM 5-NITRO-3-PHENYL-4,5-DIHYDROISOXAZOLE: DFT COMPUTATIONAL STUDY

Agnieszka Łapczuk-Krygier, Jolanta Jaśkowska, Radomir Jasiński
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Abstract


The molecular mechanism of nitrous acid elimination from 5-nitro-3-phenyl-4,5-dihydroisoxazole systems has been explored using DFT computational study. It was found that under both catalytic and non-catalytic conditions, these processes proceed according to a one-step asynchronous mechanism. The asynchronicity of transition state is determined by presence of Lewis acid catalyst. However, it is not enough to force an ionic mechanism. The proposed pattern can be considered as a general mechanism for this group of heterocyclic compounds.

Keywords


isoxazoles, nitrous acid elimination, DFT study, mechanism.

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