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Kunetskiy RA, Císarová I, Saman D, et al. New lipophilic 2-amino-N,N'-dialkyl-4,5-dimethylimidazolium cations: synthesis, structure, properties, and outstanding thermal stability in alkaline media. Chemistry. 2009;15(37):9477-85doi: 10.1002/chem.200901203.
Kunetskiy, R. A., Císarová, I., Saman, D., & Lyapkalo, I. M. (2009). New lipophilic 2-amino-N,N'-dialkyl-4,5-dimethylimidazolium cations: synthesis, structure, properties, and outstanding thermal stability in alkaline media. Chemistry (Weinheim an der Bergstrasse, Germany), 15(37), 9477-85. https://doi.org/10.1002/chem.200901203
Kunetskiy, Roman A, et al. "New lipophilic 2-amino-N,N'-dialkyl-4,5-dimethylimidazolium cations: synthesis, structure, properties, and outstanding thermal stability in alkaline media." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 15,37 (2009): 9477-85. doi: https://doi.org/10.1002/chem.200901203
Kunetskiy RA, Císarová I, Saman D, Lyapkalo IM. New lipophilic 2-amino-N,N'-dialkyl-4,5-dimethylimidazolium cations: synthesis, structure, properties, and outstanding thermal stability in alkaline media. Chemistry. 2009 Sep 21;15(37):9477-85. doi: 10.1002/chem.200901203. PMID: 19655354.
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Chemistry. 2009 Sep 21;15(37):9477-85. doi: 10.1002/chem.200901203.

New lipophilic 2-amino-N,N'-dialkyl-4,5-dimethylimidazolium cations: synthesis, structure, properties, and outstanding thermal stability in alkaline media.

Chemistry (Weinheim an der Bergstrasse, Germany)

Roman A Kunetskiy, Ivana Císarová, David Saman, Ilya M Lyapkalo

Affiliations

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6, Czech Republic.

PMID: 19655354 DOI: 10.1002/chem.200901203

Abstract

A series of new N,N'-dialkyl-4,5-dimethylimidazolium cations possessing electron-rich 2-imidazolylidene- or phosphoranylidene-amino substituents has been efficiently synthesized from common precursors, N,N'-dialkyl-4,5-dimethylimidazol-2-ylidenes. The new lipophilic salts obtained have been found to be highly stable towards strong alkali under both biphasic and homogeneous conditions. Their exceptional aqueous base resistance, which has hitherto only been seen with peralkylated polyaminophosphazenium cations, may be attributed to three factors: aromatic stabilization, efficient resonance charge delocalization, and steric protection of the exocyclic nitrogen linkage due to bulky lipophilic N-alkyl substituents.

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