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Hulla, Martin ; Chamam, Sami M. A. ; Laurenczy, Gabor ; Das, Shoubhik ; Dyson, Paul J.:
Delineating the Mechanism of Ionic Liquids in the Synthesis of Quinazoline-2,4(1H ,3H )-dione from 2-Aminobenzonitrile and CO₂.
In: Angewandte Chemie International Edition.
Bd. 56
(2017)
Heft 35
.
- S. 10559-10563.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.201705438
Abstract
Ionic liquids (ILs) are versatile solvents and catalysts for the synthesis of quinazoline-2,4-dione from 2-aminobenzonitrile and CO2. However, the role of the IL in this reaction is poorly understood. Consequently, we investigated this reaction and showed that the IL cation does not play a significant role in the activation of the substrates, and instead plays a secondary role in controlling the physical properties of the IL. A linear relationship between the pKa of the IL anion (conjugate acid) and the reaction rate was identified with maximum catalyst efficiency observed at a pKa of >14.7 in DMSO. The base-catalyzed reaction is limited by the acidity of the quinazoline-2,4-dione product, which is deprotonated by more basic catalysts, leading to the formation of the quinazolide anion (conjugate acid pKa 14.7). Neutralization of the original catalyst and formation of the quinazolide anion catalyst leads to the observed reaction limit.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Institutionen der Universität: | Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie Fakultäten Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Organische Chemie I > Lehrstuhl Organische Chemie I - Univ.-Prof. Dr. Das Shoubhik Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Organische Chemie I |
| Titel an der UBT entstanden: | Nein |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 20 Jul 2023 07:11 |
| Letzte Änderung: | 08 Nov 2023 11:23 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/86209 |