Azolium-based systems: application of an anion exchange resin (A- form) method and 1H NMR analysis of the charged-assisted (C–H)+•anion hydrogen bonds

The counteranion exchange of quaternary 1,2,3-triazolium salts was examined using a simple method that permitted halide ions to be swap for a variety of anions using an anion exchange resin (A¯ form). The method was applied to 1,2,3-triazolium-based ionic liquids and the iodideto- anion exchange pro...

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Bibliographic Details
Published in:ARKIVOC 2013-08, Vol.2014 (2), p.85-102
Main Authors: Dinares, Immaculada, Mesquida, Neus, Ibáñez, Anna, Alcalde, Ermitas
Format: Article
Language:English
Subjects:
Compostos heterocíclics
Heterocyclic compounds
Hidrogen
Hydrogen
Imidazoles
Ion exchange resins
Ionic solutions
Resines de bescanvi iònic
Sals
Salts
Solucions iòniques
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Summary:The counteranion exchange of quaternary 1,2,3-triazolium salts was examined using a simple method that permitted halide ions to be swap for a variety of anions using an anion exchange resin (A¯ form). The method was applied to 1,2,3-triazolium-based ionic liquids and the iodideto- anion exchange proceeded in excellent to quantitative yields, concomitantly removing halide impurities. Additionally, an anion exchange resin (N3¯ form) was used to obtain the benzyl azide from benzyl halide under mild reaction. Likewise, following a similar protocol, bis(azidomethyl)arenes were also synthesized in excellent yields. The results of a proton NMR spectroscopic study of simple azolium-based ion pairs are discussed, with attention focused on the significance of the charged-assisted (CH)+···anion hydrogen bonds of simple azolium systems such as 1-butyl-3-methylimidazolium and 1-benzyl-3-methyl-1,2,3-triazolium salts.
ISSN:1551-7012
1551-7004
1551-7012
DOI:10.3998/ark.5550190.p008.203