The reaction mechanism of 1,3-dipolar cycloadditions of both symmetric and unsymmetric benzo-condensed diazines with a nitrilimine dipole, to give two different mono- and bis-cycloadducts, in tetrahydrofuran (THF) solution, was studied by DFT calculatio ns. The results obtained show that each 1,3-dipolar cycloaddition reaction always proceeds by a two steps mechanism, in which the first intermediate shows only one covalent bond between the beta carbon of the nitrilimine and the aromatic nitrogen of the diazine molecule. The structure and energy content of the two transition states of the two cycloaddition steps, in the case of the unsymmetric benzo-condensed diazine, nicely explains why the product of the bis-cycloaddi tions is exclusively observed and why the product of a mono-cycloaddition is not isolated for the symmetric reaction pathway.
|Numero di pagine||7|
|Rivista||Computational and Theoretical Chemistry|
|Stato di pubblicazione||Published - 2013|
All Science Journal Classification (ASJC) codes
- Condensed Matter Physics
- Physical and Theoretical Chemistry