Understanding the regioselectivity and the molecular mechanism of [3 + 2] cycloaddition reactions between nitrous oxide and conjugated nitroalkenes: a DFT computational study
Authors:
- Ewa Dresler,
- Aneta Wróblewska,
- Radomir Jasiński
Abstract
Regiochemical aspects and the molecular mechanism of the [3 + 2] cycloaddition between nitrous oxide and conjugated nitroalkenes were evaluated on the basis of the wb97xd/6-311 + G(d) (PCM) computational study. It was found that, independently of the nature of the nitroalkene, all considered processes are realized via polar, single-step mechanisms. All attempts at the localization of hypothetical zwitterionic intermediates were unsuccessful. Additionally, the DFT computational study suggested that, in the course of the reaction, the formation of respective Δ2-4-nitro-4-R1-5-R2-1-oxa-2,3-diazolines was preferred from the kinetic point of view.
- Record ID
- CUT4d2e0e24b96b4354a94ff8b5cfb7d549
- Publication categories
- ;
- Author
- Journal series
- Molecules, ISSN , e-ISSN 1420-3049, Biweekly
- Issue year
- 2022
- Vol
- 27
- No
- 23
- Pages
- [1-9]
- Article number
- 8441
- Other elements of collation
- rys.; schem.; tab.; wykr.; Bibliografia (na s.) - 8-9; Bibliografia (liczba pozycji) - 34; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 27, Iss. 23
- Substantive notes
- Special Issue: Five and Six-Membered Heterocyclic Compounds and Their Therapeutic Potential
- Keywords in English
- [3 + 2] cycloaddition, nitrous oxide, nitroalkenes, molecular mechanism, molecular electron density theory, conceptual density functional theory
- ASJC Classification
- DOI
- DOI:10.3390/molecules27238441 Opening in a new tab
- URL
- https://www.mdpi.com/1420-3049/27/23/8441 Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 140
- Score source
- journalList
- Score
- Publication indicators
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT4d2e0e24b96b4354a94ff8b5cfb7d549/
- URN
urn:pkr-prod:CUT4d2e0e24b96b4354a94ff8b5cfb7d549
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.