Hydroxy-1H-imidazole-3-oxides - Synthesis, kinetic acidity, and application in catalysis and supramolecular anion recognition

Beitrag in einer Fachzeitschrift
(Originalarbeit)


Details zur Publikation

Autor(en): Bartz S, Blumenröder B, Kern A, Fleckenstein J, Frohnapfel S, Schatz J, Wagner A
Zeitschrift: Zeitschrift für Naturforschung Section B-A Journal of Chemical Sciences
Verlag: Verlag der Zeitschrift Fuer Naturforschung
Jahr der Veröffentlichung: 2009
Band: 64
Heftnummer: 6
Seitenbereich: 629-638
ISSN: 0932-0776


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.



FAU-Autoren / FAU-Herausgeber

Bartz, Susan
Graduiertenzentrum der FAU
Blumenröder, Bettina
Lehrstuhl für Organische Chemie I
Schatz, Jürgen Prof. Dr.
Professur für Organische Chemie


Autor(en) der externen Einrichtung(en)
Ludwig-Maximilians-Universität (LMU)


Zitierweisen

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.

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Zuletzt aktualisiert 2019-15-04 um 21:50