The molecular mechanism of the formation of four-membered cyclic nitronates and their retro (3+2) cycloaddition: a DFT mechanistic study
Authors:
- Agnieszka Kącka-Zych
Abstract
In the present work, the formation of the four-membered cyclic nitronates and the retro (3+2) cycloaddition (retro-32CA) reaction of the 4H-[1,2]oxazete 2-oxide were studied using density functional theory method at the MPWB1K/6-311G(d,p) theoretical level. The electronic structure of 3-tert-butyl-4,4-dimethyl-1,2-dinitro-pent-2-ene was known through electron localization function analysis, natural population analysis and the molecular electrostatic potential analysis. The formation of 4,4-di-tert-butyl-3-nitromethyl-4H-[1,2]oxazete 2-oxide proceed through one-step mechanism. The mechanism of the retro-32CA leading to di-tert-butyl ketone and nitrile oxide derivative should be described as an asynchronous two-stage one-step process. The bonding evolution theory study was carried out to clarify the mechanisms of the formation of 4H-[1,2]oxazete 2-oxide and their retro-32CA.
- Record ID
- CUTad057161e1494811b7d180f4c099c501
- Publication categories
- ;
- Author
- Journal series
- Molecules, ISSN , e-ISSN 1420-3049, Biweekly
- Issue year
- 2021
- Vol
- 26
- No
- 16
- Pages
- [1-12]
- Article number
- 4786
- Other elements of collation
- rys.; schem.; tab.; wykr.; Bibliografia (na s.) - 11-12; Bibliografia (liczba pozycji) - 35; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 26, Iss. 16
- Substantive notes
- Section: Computational and Theoretical Chemistry
- Keywords in English
- four-membered cyclic nitronates, molecular mechanism, density functional theory, Molecular Electron Density Theory
- DOI
- DOI:10.3390/molecules26164786 Opening in a new tab
- URL
- https://www.mdpi.com/1420-3049/26/16/4786 Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 140
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTad057161e1494811b7d180f4c099c501/
- URN
urn:pkr-prod:CUTad057161e1494811b7d180f4c099c501
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