A molecular electron density theory study of the Lewis acid–catalyzed decomposition reaction of nitroethyl benzoate using aluminum derivatives
Authors:
- Agnieszka Kącka-Zych,
- Mar Ríos‐Gutiérrez,
- Luis R. Domingo
Abstract
The molecular mechanism of the decomposition reaction of nitroethyl benzoate (NEB‐1) catalyzed by Lewis acids (LAs) based on aluminum metal, AlMe3, and AlCl3, in N,N‐dimethylacetamide, has been analyzed within the molecular electron density theory (MEDT) using calculations at the B3LYP(PCM)/6‐31+G(d) computational level. These LA‐catalyzed decomposition reactions take place via a two‐step mechanism involving a zwitterionic intermediate. The use of a more acidic AlCl3 LA favors the decomposition reaction, both kinetically and thermodynamically. The bonding evolution theory (BET) analyses indicate that these LA‐catalyzed decomposition reactions begin with the proton transfer process, followed by the extrusion of benzoic acid at the second step of the reaction.
- Record ID
- CUT659f2dfc5e3f48c7898f8006a6bca965
- Publication categories
- ;
- Author
- Journal series
- Journal of Physical Organic Chemistry, ISSN 0894-3230, e-ISSN 1099-1395, [1099-1395]
- Issue year
- 2019
- Vol
- 32
- No
- 6
- Pages
- [1-12]
- Article number
- e3938
- Other elements of collation
- schem.; tab.; wykr.; Bibliografia (na s.) - 11-12; Bibliografia (liczba pozycji) - 32; Oznaczenie streszczenia - Abstr.; Data udostępnienia on-line - 2019-02-25; Numeracja w czasopiśmie - Vol. 32, Iss. 6
- Keywords in English
- aluminum catalyst, bonding evolution theory, decomposition reaction, electron localization function, Lewis acid catalysis, molecular electron density theory, nitroalkenes
- DOI
- DOI:10.1002/poc.3938 Opening in a new tab
- URL
- https://onlinelibrary.wiley.com/doi/full/10.1002/poc.3938 Opening in a new tab
- Related project
- Teoretyczne badania nad zastosowaniem przyjaznych środowisku technik do otrzymywania bioaktywnych nitrozwiązków - potencjalnych farmaceutyków. . Project leader at PK: , ,
- Language
- eng (en) English
- Score (nominal)
- 40
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT659f2dfc5e3f48c7898f8006a6bca965/
- URN
urn:pkr-prod:CUT659f2dfc5e3f48c7898f8006a6bca965
* 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.