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Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities

Peter Nockemann, Ben Thijs, Kris Driesen, Colin Janssen UGent, Kristof Van Hecke UGent, Luc Van Meervelt, Simone Kossmann, Barbara Kichner and Koen Binnemans (2007) JOURNAL OF PHYSICAL CHEMISTRY B. 111(19). p.5254-5263
abstract
Choline saccharinate and choline acesulfamate are two examples of hydrophilic ionic liquids, which can be prepared from easily available starting materials (choline chloride and a non-nutritive sweetener). The (eco)toxicity of these ionic liquids in aqueous solution is very low in comparison to other types of ionic liquids. A general method for the synthesis and purification of hydrophilic ionic liquids is presented. The method consists of a silver-free metathesis reaction, followed by purification of the ionic liquid by ion-exchange chromatography. The crystal structures show a marked difference in hydrogen bonding between the two ionic liquids, although the saccharinate and the acesulfamate anions show structural similarities. The optimized structures, the energetics, and the charge distribution of cation-anion pairs in the ionic liquids were studied by density functional theory (DFT) and second-order (Moller-Plesset) perturbation theory calculations. The occupation of the non-Lewis orbitals was considered to obtain a qualitative picture of the Lewis structures. The calculated interaction energies and the dipole moments for the ion pairs in the gas phase were discussed.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
GAS-CHROMATOGRAPHY, ELECTRONIC-STRUCTURE CALCULATIONS, STATIONARY PHASES, DAPHNIA-MAGNA, INTERMOLECULAR INTERACTIONS, CONFORMATIONAL EQUILIBRIUM, CATALYTIC REACTIONS, METHYL-SULFATE, POPULATION ANALYSIS, MOLECULAR-DYNAMICS
journal title
JOURNAL OF PHYSICAL CHEMISTRY B
J. Phys. Chem. B
volume
111
issue
19
pages
5254 - 5263
Web of Science type
Article
Web of Science id
000246341300032
JCR category
CHEMISTRY, PHYSICAL
JCR impact factor
4.086 (2007)
JCR rank
19/107 (2007)
JCR quartile
1 (2007)
ISSN
1520-6106
DOI
10.1021/jp068446a
language
English
UGent publication?
yes
classification
A1
id
388778
handle
http://hdl.handle.net/1854/LU-388778
date created
2008-02-26 14:54:00
date last changed
2012-03-21 15:34:08
@article{388778,
  abstract     = {Choline saccharinate and choline acesulfamate are two examples of hydrophilic ionic liquids, which can be prepared from easily available starting materials (choline chloride and a non-nutritive sweetener). The (eco)toxicity of these ionic liquids in aqueous solution is very low in comparison to other types of ionic liquids. A general method for the synthesis and purification of hydrophilic ionic liquids is presented. The method consists of a silver-free metathesis reaction, followed by purification of the ionic liquid by ion-exchange chromatography. The crystal structures show a marked difference in hydrogen bonding between the two ionic liquids, although the saccharinate and the acesulfamate anions show structural similarities. The optimized structures, the energetics, and the charge distribution of cation-anion pairs in the ionic liquids were studied by density functional theory (DFT) and second-order (Moller-Plesset) perturbation theory calculations. The occupation of the non-Lewis orbitals was considered to obtain a qualitative picture of the Lewis structures. The calculated interaction energies and the dipole moments for the ion pairs in the gas phase were discussed.},
  author       = {Nockemann, Peter and Thijs, Ben and Driesen, Kris and Janssen, Colin and Van Hecke, Kristof and Van Meervelt, Luc and Kossmann, Simone and Kichner, Barbara and Binnemans, Koen},
  issn         = {1520-6106},
  journal      = {JOURNAL OF PHYSICAL CHEMISTRY B},
  keyword      = {GAS-CHROMATOGRAPHY,ELECTRONIC-STRUCTURE CALCULATIONS,STATIONARY PHASES,DAPHNIA-MAGNA,INTERMOLECULAR INTERACTIONS,CONFORMATIONAL EQUILIBRIUM,CATALYTIC REACTIONS,METHYL-SULFATE,POPULATION ANALYSIS,MOLECULAR-DYNAMICS},
  language     = {eng},
  number       = {19},
  pages        = {5254--5263},
  title        = {Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities},
  url          = {http://dx.doi.org/10.1021/jp068446a},
  volume       = {111},
  year         = {2007},
}

Chicago
Nockemann, Peter, Ben Thijs, Kris Driesen, Colin Janssen, Kristof Van Hecke, Luc Van Meervelt, Simone Kossmann, Barbara Kichner, and Koen Binnemans. 2007. “Choline Saccharinate and Choline Acesulfamate: Ionic Liquids with Low Toxicities.” Journal of Physical Chemistry B 111 (19): 5254–5263.
APA
Nockemann, P., Thijs, B., Driesen, K., Janssen, C., Van Hecke, K., Van Meervelt, L., Kossmann, S., et al. (2007). Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities. JOURNAL OF PHYSICAL CHEMISTRY B, 111(19), 5254–5263.
Vancouver
1.
Nockemann P, Thijs B, Driesen K, Janssen C, Van Hecke K, Van Meervelt L, et al. Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities. JOURNAL OF PHYSICAL CHEMISTRY B. 2007;111(19):5254–63.
MLA
Nockemann, Peter, Ben Thijs, Kris Driesen, et al. “Choline Saccharinate and Choline Acesulfamate: Ionic Liquids with Low Toxicities.” JOURNAL OF PHYSICAL CHEMISTRY B 111.19 (2007): 5254–5263. Print.