An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate
Abstract 1,3‐Dimethylimidazolium‐2‐carboxylate and carbonic acid have been used to prepare a 1,3‐dimethylimidazolium hydrogen carbonate salt by means of a Krapcho reaction. The ability to form hydrogen carbonate azolium salts allows for them to be used as precursors for fast, efficient, environmenta...
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crwiley:10.1002/chem.200700055 2024-06-23T07:52:03+00:00 An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate Bridges, Nicholas J. Hines, C. Corey Smiglak, Marcin Rogers, Robin D. 2007 http://dx.doi.org/10.1002/chem.200700055 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.200700055 https://onlinelibrary.wiley.com/doi/full/10.1002/chem.200700055 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chemistry – A European Journal volume 13, issue 18, page 5207-5212 ISSN 0947-6539 1521-3765 journal-article 2007 crwiley https://doi.org/10.1002/chem.200700055 2024-06-06T04:24:20Z Abstract 1,3‐Dimethylimidazolium‐2‐carboxylate and carbonic acid have been used to prepare a 1,3‐dimethylimidazolium hydrogen carbonate salt by means of a Krapcho reaction. The ability to form hydrogen carbonate azolium salts allows for them to be used as precursors for fast, efficient, environmentally benign, and halide‐free syntheses of many ionic liquids by a simple, acid–base reaction of virtually any acid (inorganic, organic, and organic noncarboxylic) with a p K a less than that of HCO 3 − . Additionally, the kinetics of this reaction can be accelerated by employing catalytic amounts of DMSO (a traditional Krapcho solvent used in decarboxylation reactions) to catalyze the decarboxylation. The crystal structure of 1,3‐dimethylimidazolium hydrogen carbonate monohydrate is the first example of an imidazolium‐based hydrogen carbonate salt. There is a strong 2D hydrogen‐bonded network with facially π‐stacked imidazolium cations located in the cavities created by this framework. Article in Journal/Newspaper Carbonic acid Wiley Online Library Chemistry – A European Journal 13 18 5207 5212 |
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Wiley Online Library |
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English |
description |
Abstract 1,3‐Dimethylimidazolium‐2‐carboxylate and carbonic acid have been used to prepare a 1,3‐dimethylimidazolium hydrogen carbonate salt by means of a Krapcho reaction. The ability to form hydrogen carbonate azolium salts allows for them to be used as precursors for fast, efficient, environmentally benign, and halide‐free syntheses of many ionic liquids by a simple, acid–base reaction of virtually any acid (inorganic, organic, and organic noncarboxylic) with a p K a less than that of HCO 3 − . Additionally, the kinetics of this reaction can be accelerated by employing catalytic amounts of DMSO (a traditional Krapcho solvent used in decarboxylation reactions) to catalyze the decarboxylation. The crystal structure of 1,3‐dimethylimidazolium hydrogen carbonate monohydrate is the first example of an imidazolium‐based hydrogen carbonate salt. There is a strong 2D hydrogen‐bonded network with facially π‐stacked imidazolium cations located in the cavities created by this framework. |
format |
Article in Journal/Newspaper |
author |
Bridges, Nicholas J. Hines, C. Corey Smiglak, Marcin Rogers, Robin D. |
spellingShingle |
Bridges, Nicholas J. Hines, C. Corey Smiglak, Marcin Rogers, Robin D. An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate |
author_facet |
Bridges, Nicholas J. Hines, C. Corey Smiglak, Marcin Rogers, Robin D. |
author_sort |
Bridges, Nicholas J. |
title |
An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate |
title_short |
An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate |
title_full |
An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate |
title_fullStr |
An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate |
title_full_unstemmed |
An Intermediate for the Clean Synthesis of Ionic Liquids: Isolation and Crystal Structure of 1,3‐Dimethylimidazolium Hydrogen Carbonate Monohydrate |
title_sort |
intermediate for the clean synthesis of ionic liquids: isolation and crystal structure of 1,3‐dimethylimidazolium hydrogen carbonate monohydrate |
publisher |
Wiley |
publishDate |
2007 |
url |
http://dx.doi.org/10.1002/chem.200700055 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.200700055 https://onlinelibrary.wiley.com/doi/full/10.1002/chem.200700055 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
Chemistry – A European Journal volume 13, issue 18, page 5207-5212 ISSN 0947-6539 1521-3765 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chem.200700055 |
container_title |
Chemistry – A European Journal |
container_volume |
13 |
container_issue |
18 |
container_start_page |
5207 |
op_container_end_page |
5212 |
_version_ |
1802643249325670400 |