Regioselectivity, stereoselectivity, and molecular mechanism of [3 + 2] cycloaddition reactions between 2-methyl-1-nitroprop-1-ene and (Z)-C-aryl-N-phenylnitrones: a DFT computational study
Authors:
- Ewa Dresler,
- Agnieszka Kącka-Zych,
- Magdalena Kwiatkowska,
- Radomir Jasiński
Abstract
Reaction paths for [3 + 2] cycloaddition (32CA) between 2-methyl-1-nitroprop-1-ene and (Z)-C-aryl-N-phenylnitrones were explored in detail at the B3LYP/6-31G(d) level of theory. All of the 32CA processes considered were found to be initiated by the attack of the most nucleophilic oxygen atom in the nitrone molecule on the most electrophilic carbon atom (Cβ) in the nitroethylene moiety. This type of interaction favors the formation of 4-nitro-substituted cycloadducts. Additionally, based on a molecular electron density theory (MEDT) study, the 32CA processes of interest should be considered polar processes with asynchronous transition states (TSs). However, the asynchronicity of the localized TSs is unexpectedly low and clearly insufficient to enforce a stepwise zwitterionic mechanism.
- Record ID
- CUT4c8095ac797f4ed08fd70dbc78650d63
- Publication categories
- ;
- Author
- Journal series
- Journal of Molecular Modeling, ISSN 1610-2940, e-ISSN 0948-5023
- Issue year
- 2018
- Vol
- 24
- No
- 11
- Pages
- [1-12]
- Other elements of collation
- schem.; tab.; wykr.; Bibliografia (na s.) - 10-12; Bibliografia (liczba pozycji) - 58; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 24, Iss. 11
- Keywords in English
- [3 + 2] cycloaddition, nitrone, nitroalkene, DFTstudy, molecular electron density theory, mechanism
- DOI
- DOI:10.1007/s00894-018-3861-y Opening in a new tab
- URL
- https://link-1springer-1com-108j34ijl1142.han.biblos.pk.edu.pl/article/10.1007%2Fs00894-018-3861-y Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 25
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT4c8095ac797f4ed08fd70dbc78650d63/
- URN
urn:pkr-prod:CUT4c8095ac797f4ed08fd70dbc78650d63
* 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.