The structural aspects of the transformation of 3-nitroisoxazoline-2-oxide to 1-aza-2,8-dioxabicyclo[3.3.0]octane derivatives: Experimental and MEDT theoretical study
Authors:
- Przemysław Woliński,
- Agnieszka Kącka-Zych,
- Błażej Dziuk,
- Krzysztof Ejsmont,
- Agnieszka Łapczuk-Krygier,
- Ewa Dresler
Abstract
Reaction of 3-nitroisoxazoline-2-oxide with monosubstituted ethenes, first time documented fifty years ago, have been reviewed. Structures of phenyl and cyano derivatives of 1-aza-2,8-dioxabicyclo[3.3.0]octane produced in [3 + 2] cycloaddition (32CA) between styrene and acrylonitrile with 3-nitroisoxazoline-2-oxide were determined through single crystal XRD analysis. The molecular mechanism of the title 32CA has been also analyzed within the Molecular Electron Density Theory (MEDT) based on the M06-2X(PCM)/6-311 + G(d,p) calculations.
- Record ID
- CUT7ef83868fe1640ea9be5597813c7a92a
- Publication categories
- ;
- Author
- Journal series
- Journal of Molecular Structure, ISSN 0022-2860, e-ISSN 1872-8014
- Issue year
- 2019
- Vol
- 1192
- Pages
- 27-34
- Other elements of collation
- schem.; tab.; wykr.; Bibliografia (na s.) - 33-34; Bibliografia (liczba pozycji) - 47; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 1192
- Keywords in English
- 3-nitroisoxazoline-2-oxide(3+2) cycloadditionMolecular electron density theoryElectron localization functionXRD analysis
- DOI
- DOI:10.1016/j.molstruc.2019.04.061 Opening in a new tab
- URL
- https://www.sciencedirect.com/science/article/pii/S0022286019304624 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 70
- Publication indicators
- Citation count
- 16
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT7ef83868fe1640ea9be5597813c7a92a/
- URN
urn:pkr-prod:CUT7ef83868fe1640ea9be5597813c7a92a
* 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.