Issue 1, 2006

Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling

Abstract

Using previously published toxicity data as well as a small set of heretofore-unpublished results, quantitative structure–property relationship models are developed to assess the factors that govern the toxicity of a range of different ionic liquids to two aquatic organisms (Vibrio fischeri and Daphnia magna). With at most four molecular descriptors, log10 EC50 and log10 LC50 data are reproduced with an R2 of 0.78–0.88. Besides the well-established link between toxicity and alkyl chain length on imidazolium, pyridinium and quaternary ammonium-based ionic liquids, the models predict that toxicity increases slightly with the number of nitrogen atoms in an aromatic cation ring. All other things being equal, toxicity is expected to show the trend with cation type of ammonium < pyridinium < imidazolium < triazolium < tetrazolium. In addition, toxicity is expected to decrease with ring methylation as well as with an increase in the number of negatively charged atoms on the cation. The anion plays a secondary role in toxicity for the compounds studied here, although the presence of positively charged atoms on the anion are predicted to slightly increase toxicity.

Graphical abstract: Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling

Article information

Article type
Paper
Submitted
08 Aug 2005
Accepted
01 Nov 2005
First published
30 Nov 2005

Green Chem., 2006,8, 82-90

Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling

D. J. Couling, R. J. Bernot, K. M. Docherty, J. K. Dixon and E. J. Maginn, Green Chem., 2006, 8, 82 DOI: 10.1039/B511333D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements