at Google ScholarTitle data
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.
Vol. 56
(2017)
Issue 35
.
- pp. 10559-10563.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.201705438
Abstract in another language
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.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I > Chair Organic Chemistry I - Univ.-Prof. Dr. Das Shoubhik Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 20 Jul 2023 07:11 |
| Last Modified: | 08 Nov 2023 11:23 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/86209 |