Hydroxy-1H-imidazole-3-oxides - Synthesis, kinetic acidity, and application in catalysis and supramolecular anion recognition
Bartz S, Blumenröder B, Kern A, Fleckenstein J, Frohnapfel S, Schatz J, Wagner A (2009)
Publication Type: Journal article, Original article
Publication year: 2009
Journal
Original Authors: Bartz S., Blumenröder B., Kern A., Fleckenstein J., Frohnapfel S., Schatz J., Wagner A.
Publisher: Verlag der Zeitschrift Fuer Naturforschung
Book Volume: 64
Pages Range: 629-638
Journal Issue: 6
URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-67749143949&origin=inward
Abstract
Using ab initio calculations (B3LYP 6-31G) the geometries of diethyl, dimethoxy and dimethylamino imidazolium salts were studied as representative models of imidazolium salts bearing heteroatoms directly attached to the ring nitrogen atoms of the imidazolium core units. In all cases the syn and anti arrangement of the substituents could be identified. In addition to the theoretical studies, eleven dialkoxy imidazolium salts were prepared by alkylation of six 1-hydroxy-imidazole-3-oxides using dimethyl or diethyl sulfate as strong alkylating reagents. The kinetic acidities of these compounds were studied by measuring the pseudo-first order reaction rates of the H/D exchange process of the C2-H proton of compounds 3-9. The observed kinetic acidities are much higher than reaction rates observed for simple imidazolium salts; half-lifes of the H/D exchange are usually in the range of minutes. Similar to dialkyl/aryl imidazolium salts, all prepared dialkoxy imidazolium salts could be used as precatalysts in standard aqueous Suzuki coupling reactions. In addition, two representative dialkoxy imidazolium salts could be used in supramolecular anion recognition, as demonstrated by binding studies towards iodide as guest. © 2009 Verlag der Zeitschrift für Naturforschung, Tübingen.
Authors with CRIS profile
Susan Bartz
Graduiertenzentrum der FAU
Bettina Blumenröder
Lehrstuhl für Organische Chemie I
Jürgen Schatz
Professur für Organische Chemie
Involved external institutions
Germany (DE)How to cite
APA:
Bartz, S., Blumenröder, B., Kern, A., Fleckenstein, J., Frohnapfel, S., Schatz, J., & Wagner, A. (2009). Hydroxy-1H-imidazole-3-oxides - Synthesis, kinetic acidity, and application in catalysis and supramolecular anion recognition. Zeitschrift für Naturforschung Section B-A Journal of Chemical Sciences, 64(6), 629-638.
MLA:
Bartz, Susan, et al. "Hydroxy-1H-imidazole-3-oxides - Synthesis, kinetic acidity, and application in catalysis and supramolecular anion recognition." Zeitschrift für Naturforschung Section B-A Journal of Chemical Sciences 64.6 (2009): 629-638.
BibTeX: Download