Mechanistic aspects of the synthesis of seven-membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes: molecular electron density theory computational study
Authors:
- Agnieszka Kącka-Zych,
- Radomir Jasiński
Abstract
The density functional theory computational study indicates the possibility of the synthesis of seven-membered internal nitronates via cycloaddition reactions involving Z-C-aryl-N-methylnitrones and E-2-aryl-1-cyano-1-nitroethenes. The detailed exploration of the reaction paths indicates a polar, stepwise reaction mechanism through the zwitterionic intermediate. Using bonding evolution theory (BET), we have deciphered the molecular mechanism of the [4 + 3] cycloaddition reaction between E-2-phenyl-1-cyano-1-nitroethene and Z-C-phenyl-N-methylnitrone. The BET study has revealed that the formation of two C-O single bonds takes place in the same way, through the depopulation of N-C and C-C bonding regions and monosynaptic basins, respectively. The first O1-C7 single bond was formed in the sixth phase, while the second C3-O4 bond was formed in the last ninth phase.
- Record ID
- CUT14d653cd4c69416193fd0343190068d4
- Publication categories
- ;
- Author
- Journal series
- Journal of Computational Chemistry, ISSN 0192-8651, e-ISSN 1096-987X, Annual
- Issue year
- 2022
- Vol
- 43
- No
- 18
- Pages
- 1221-1228
- Other elements of collation
- rys.; tab.; wykr.; Bibliografia (na s.) - 1228; Bibliografia (liczba pozycji) - 54; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 43, Iss. 18
- Keywords in English
- [4+3] cycloaddition reaction, molecular electron density theory, nitroalkenes, nitronates, mechanism
- ASJC Classification
- ;
- DOI
- DOI:10.1002/jcc.26885 Opening in a new tab
- URL
- https://onlinelibrary.wiley.com/doi/10.1002/jcc.26885 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 100
- Score source
- journalList
- Score
- Publication indicators
- Citation count
- 8
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT14d653cd4c69416193fd0343190068d4/
- URN
urn:pkr-prod:CUT14d653cd4c69416193fd0343190068d4
* 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.