Journal of Molecular Graphics and Modelling, volume 101, pages 107714
Molecular mechanism of Hetero Diels-Alder reactions between (E)-1,1,1-trifluoro-3-nitrobut-2-enes and enamine systems in the light of Molecular Electron Density Theory
Publication type: Journal Article
Publication date: 2020-12-01
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.9
ISSN: 10933263, 18734243
Materials Chemistry
Physical and Theoretical Chemistry
Spectroscopy
Computer Graphics and Computer-Aided Design
Abstract
The molecular mechanism of the reaction of (E)-1,1,1-trifluoro-3-nitrobut-2-ene 1 with 3,3-dimethyl-2-morpholinobutene 2 has been studied within the Molecular Electron Density Theory (MEDT). This theoretical study confirm the possibility of the formation of zwitterionic structures in the first reaction stage. Interestingly, that localized zwitterions are however not common intermediates for identified in the postreaction mixture products. The further Bonding Evolution Theory (BET) study show, that the key, HDA reaction takes place in one-step but in a non-concerted manner since three stages are clearly identified. First the C5-C6 double bond breaks, then the C1-C2 bond breaks, and in the last phase we observed the formation of the C1-C6 single bond and V(C2) and V' (C2) pseudoradical centers in Z1 molecule. In turn, the molecular mechanism of the conversion of zwitterion Z1 to product 3 can be divided also in three groups in which we observed the disappearance of the two pseudoradical centers and formation O4-C5 single and C3-N3 double bonds, respectively.
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Kącka Zych A., Jasiński R. Molecular mechanism of Hetero Diels-Alder reactions between (E)-1,1,1-trifluoro-3-nitrobut-2-enes and enamine systems in the light of Molecular Electron Density Theory // Journal of Molecular Graphics and Modelling. 2020. Vol. 101. p. 107714.
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Kącka Zych A., Jasiński R. Molecular mechanism of Hetero Diels-Alder reactions between (E)-1,1,1-trifluoro-3-nitrobut-2-enes and enamine systems in the light of Molecular Electron Density Theory // Journal of Molecular Graphics and Modelling. 2020. Vol. 101. p. 107714.
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TY - JOUR
DO - 10.1016/j.jmgm.2020.107714
UR - https://doi.org/10.1016/j.jmgm.2020.107714
TI - Molecular mechanism of Hetero Diels-Alder reactions between (E)-1,1,1-trifluoro-3-nitrobut-2-enes and enamine systems in the light of Molecular Electron Density Theory
T2 - Journal of Molecular Graphics and Modelling
AU - Kącka Zych, Agnieszka
AU - Jasiński, Ryszard
PY - 2020
DA - 2020/12/01 00:00:00
PB - Elsevier
SP - 107714
VL - 101
SN - 1093-3263
SN - 1873-4243
ER -
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@article{2020_Kącka Zych,
author = {Agnieszka Kącka Zych and Ryszard Jasiński},
title = {Molecular mechanism of Hetero Diels-Alder reactions between (E)-1,1,1-trifluoro-3-nitrobut-2-enes and enamine systems in the light of Molecular Electron Density Theory},
journal = {Journal of Molecular Graphics and Modelling},
year = {2020},
volume = {101},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.jmgm.2020.107714},
pages = {107714},
doi = {10.1016/j.jmgm.2020.107714}
}