Understanding the large solubility of lidocaine in 1-n-butyl-3-methylimidazolium based ionic liquids using molecular simulation

Room temperature ionic liquids have been proposed as replacement solvents in a wide range of industrial separation processes. Here, we focus on the use of ionic liquids as solvents for the pharmaceutical compound lidocaine. We show that the solubility of lidocaine in seven common 1-n-butyl-3-methyli...

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Bibliographic Details
Published in:The Journal of chemical physics 2016-02, Vol.144 (8), p.084501-084501
Main Authors: Ley, Ryan T., Paluch, Andrew S.
Format: Article
Language:English
Subjects:
Functional groups
Hydrogen bonding
Imidazoles - chemistry
Imides - chemistry
Ionic liquids
Ionic Liquids - chemistry
Ions
Lidocaine - chemistry
Molecular Dynamics Simulation
Molecular Structure
Solubility
Solvents
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Summary:Room temperature ionic liquids have been proposed as replacement solvents in a wide range of industrial separation processes. Here, we focus on the use of ionic liquids as solvents for the pharmaceutical compound lidocaine. We show that the solubility of lidocaine in seven common 1-n-butyl-3-methylimidazolium based ionic liquids is greatly enhanced relative to water. The predicted solubility is greatest in [BMIM]+[CH3CO2]−, which we find results from favorable hydrogen bonding between the lidocaine amine hydrogen and the [CH3CO2]− oxygen, favorable electrostatic interactions between the lidocaine amide oxygen with the [BMIM]+ aromatic ring hydrogens, while lidocaine does not interfere with the association of [BMIM]+ with [CH3CO2]−. Additionally, by removing functional groups from the lidocaine scaffold while maintaining the important amide group, we found that as the van der Waals volume increases, solubility in [BMIM]+[CH3CO2]− relative to water increases.
ISSN:0021-9606
1089-7690
DOI:10.1063/1.4942025