Understanding the molecular mechanism of mhermal and LA-catalysed Diels–Alder reactions between cyclopentadiene and isopropyl 3-nitroprop-2-enate
Authors:
- Ewa Dresler,
- Aneta Wróblewska,
- Radomir Jasiński
Abstract
The molecular mechanism of the Diels–Alder reaction with the participation of cyclopentadiene and isopropyl 3-nitroprop-2-enate was examined based on wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was found that the type of mechanism for the conversion of addends depends significantly on the reaction conditions. In less-polar environments, a one-step polar mechanism is realised. In more polar solvents, the formation of “extended”-type zwitterionic intermediates is possible. In contrast, in the presence of an LA-type catalyst, the one-step mechanisms are replaced by respective stepwise mechanisms with zwitterionic or heterocyclic intermediates.
- Record ID
- CUT8590098904f04a1daf95dceda44f7301
- Publication categories
- ;
- Author
- Journal series
- Molecules, ISSN , e-ISSN 1420-3049, Biweekly
- Issue year
- 2023
- Vol
- 28
- No
- 14
- Pages
- [1-13]
- Article number
- 5289
- Other elements of collation
- rys.; schem.; tab.; Bibliografia (na s.) - 11-13; Bibliografia (liczba pozycji) - 49; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 28, Iss. 14
- Substantive notes
- This article belongs to the Special Issue: Computational and Theoretical Studies on Isomeric Organic Compounds
- Keywords in English
- Diels-Alder, nitroalkene
- ASJC Classification
- DOI
- DOI:10.3390/molecules28145289 Opening in a new tab
- URL
- https://www.mdpi.com/1420-3049/28/14/5289 Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 140
- Score source
- journalList
- Score
- Publication indicators
- Additional fields
- Indeksowana w: Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT8590098904f04a1daf95dceda44f7301/
- URN
urn:pkr-prod:CUT8590098904f04a1daf95dceda44f7301
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