A new insight on the molecular mechanism of the reaction between (Z)-C,N-diphenylnitrone and 1,2-bismethylene-3,3,4,4,5,5-hexamethylcyclopentane
Authors:
- Radomir Jasiński
Abstract
The molecular reaction mechanism of (Z)-C,N-diphenylnitrone and 1,2-bismethylene-3,3,4,4,5,5-hexamethylcyclopentane was verified, based on M062x/6-311 + G(d) quantumchemical calculations. It was shown that, contrary to what was postulated in earlier reports, this reaction process occurs without the intervention of a biradical intermediate. In particular, [3 + 2] cycloadducts are formed by a one-step non-polar reaction. The most likely scenario for the formation of the [3 + 4] adduct is the 1,3-sigmatropic rearrangement of the [3 + 2] adduct, or the 1,2-sigmatropic rearrangement of the Diels-Alder labile adduct. It has been shown that this mechanism can be generalised for reactions involving a broader group of 2,3-substituted buta-1,3-diene analogues.
- Record ID
- CUT737d24deb8814d48a98d31a695baca03
- Publication categories
- ;
- Author
- Journal series
- Journal of Molecular Graphics & Modelling, ISSN 1093-3263, e-ISSN 1873-4243
- Issue year
- 2020
- Vol
- 94
- Pages
- [1-5]
- Article number
- 107461
- Other elements of collation
- schem.; tab.; wykr.; Bibliografia (na s.) - 5; Bibliografia (liczba pozycji) - 28; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 94
- Keywords in English
- molecular mechanism, Cycloaddition Nitrones, DFT study, molecular electron density theory
- DOI
- DOI:10.1016/j.jmgm.2019.107461 Opening in a new tab
- URL
- https://www.sciencedirect.com/science/article/pii/S1093326319306345 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 70
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT737d24deb8814d48a98d31a695baca03/
- URN
urn:pkr-prod:CUT737d24deb8814d48a98d31a695baca03
* 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.