- Turkish Journal of Chemistry
- Vol: 37 Issue: 5
- Molecular mechanism of Diels–Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopent...
Molecular mechanism of Diels–Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene: B3LYP/6-31G(d) computational study
Authors : Radomir Jasinski, Andrzej Baranski
Pages : 848-852
Doi:10.3906/kim-1208-13
View : 9 | Download : 6
Publication Date : 9999-12-31
Article Type : Makaleler
Abstract :Analysis of reactivity indexes supports the polar character of the reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene. This is confirmed by the analysis of electronic properties of transition complexes involved in the reaction paths using the B3LYP/6-31G(d) algorithm. The transition state's asymmetry is large, but it is insufficient to provoke a zwitterionic reaction mechanism. Attempts to find a heterocyclic intermediate 7 in the reaction path ultimately leading to 5-endo-nitro-6-exo-trichloromethylnorbornene 3 have been unsuccessful.Keywords : Polar Diels--Alder reaction, mechanism, cyclopentadiene, nitroalkene, electrophilicity, nucleophilicity