A structure–activity relationship study of the toxicity of ionic liquids using an adapted Ferreira–Kiralj hydrophobicity parameter

Abstract

The Ferreira-Kiralj hydrophobicity parameter Wc is a number fraction of hydrophobic carbon atoms and can be regarded as a constitutional descriptor since its calculation depends only on the number of polar and nonpolar carbons in a compound. Hydrophobicity is important to the toxicity of ionic liquids (ILs), which are salts by nature. Herein, a descriptor for this property was calculated using a simple adaptation of the type of polar carbon atoms included (WcAdap) to explore the possibility of its use in quantitative structure-activity relationship (QSAR) studies of ILs. The resulting model was tested using a database of ILs with toxicity against the Leukemia rat cell line IPC-81. Two other models were constructed using Crippen log P and Mannhold log P descriptors, which are both available in the free program PaDEL. The use of WcAdap led to a better and more indicative model. Thus, WcAdap may be a suitable molecular descriptor for the hydrophobicity of ILs in QSAR studies.

Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine

“…Thus, cholinium ILs in general demonstrated lower cytotoxicity than ILs with other common cations, such as imidazolium and pyridinium. Several attempts to create a prediction model for assessing IL cytotoxicity in silico have been made; ,− however, at the moment, there is no possibility to distinguish the cytotoxicity of ILs only by their structure, because it also strongly depends on the external factors, such as the cell type …”

Comprehensive Interrogation on Acetylcholinesterase Inhibition by Ionic Liquids Using Machine Learning and Molecular Modeling

“…Previously, the QSAR (quantitative structure–activity relationship) modeling approach has been applied to predict the toxicity of ILs. − However, most QSAR models have been constructed by using one machine learning method. Therefore, the resulting models were limited by the power of individual approaches.…”

Cationic polymerization of p-methylstyrene in selected ionic liquids and polymerization mechanism

“…[1][2][3] Utilizing ILs is one of the goals of green chemistry because they facilitate a clean and sustainable chemistry and serve as environmentally friendly solvents for many synthetic 4-6 and catalytic 7,8 processes. [1][2][3] Utilizing ILs is one of the goals of green chemistry because they facilitate a clean and sustainable chemistry and serve as environmentally friendly solvents for many synthetic 4-6 and catalytic 7,8 processes.…”

“…Ionic liquids (ILs), as green solvents, have been studied extensively because of their attractive properties, such as negligible vapor pressure, high thermal stability, high ionic conductivity, a large electrochemical window, a broad temperature range where the substances are liquid, and ability to solvate compounds of varying polarities. [1][2][3] Utilizing ILs is one of the goals of green chemistry because they facilitate a clean and sustainable chemistry and serve as environmentally friendly solvents for many synthetic [4][5][6] and catalytic 7,8 processes.…”