Descriptors for ions and ion-pairs for use in linear free energy relationships

Abraham, Michael H.; Acree, William E.

doi:10.1016/j.chroma.2015.07.023

Cited by 62 publications

(39 citation statements)

References 100 publications

(192 reference statements)

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“…6. Values are for Na + : -8.12 (obs) (Zhang et al, 2012), -7.41 (calc) (Zhang et al, 2012) and -7.55 (this work), and for Et4N + : -7.84 (obs) (Zhang et al, 2012), -6.48 (calc) (Zhang et al, 2012) and -6.38 (this work), so that it is possible to predict log Kp for permanent ions with no more than a set of simple descriptors (Abraham and Acree, 2016).…”

Section: Resultsmentioning

confidence: 99%

“…The values of log Kp of the 247 compounds or species in our data set covers both 'highly permeable' and 'poorly permeable' values, varying from -10.01 to -3.00, and meets a normal distribution very well, with a mean of -6.027 and a standard deviation of 1.165, as seen in Figure 1. Stephens et al (2012) and Zhang et al (2012) or obtained as described before (Abraham et al, 2015a;Abraham et al, 2015b;Clarke and Mallon, 2012); ionic descriptors obtained as described before (Abraham and Acree, 2016). b Cited studies where log Kp (obs) was obtained.…”

Section: Resultsmentioning

confidence: 99%

“…We use the term "ions" for permanent ions such as Na + and Cl − , and the term "ionic species" for ions derived from protonation of basic compounds and deprotonation of acidic compounds. The compound descriptors for neutral molecules are obtained from a variety of experimental processes, as explained in a number of reviews Clarke and Mallon, 2012;Poole et al, 2013), and Abraham and Acree have reviewed the methods used to obtain descriptors for ions and ionic species (Abraham and Acree, 2016). The coefficients (c, e, s, a, b, v, j + and j -) in Eq.…”

Section: Methods Lfer Modelmentioning

confidence: 99%

“…As mentioned, we have previously constructed an equation for predicting skin permeability of neutral molecules, ions and ionic species using the Abraham linear free-energy relationship (LFER) model (Zhang et al, 2012). Since then, descriptors for considerably more compounds have been obtained, including those for ionic species (Abraham and Acree, 2016), and it is the purpose of the present work to set out an extended equation for the correlation and prediction of human skin permeability, including neutral molecules and ionic species in the same equation.…”

Section: Introductionmentioning

confidence: 99%

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An equation for the prediction of human skin permeability of neutral molecules, ions and ionic species

Zhang

Abraham

Liu

2017

International Journal of Pharmaceutics

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methods Lfer Modelmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

An equation for the prediction of human skin permeability of neutral molecules, ions and ionic species

Zhang

Abraham

Liu

2017

International Journal of Pharmaceutics

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“…For this purpose, a linear free energy relationship (LFER) model is suitable because it consists of a few descriptors with well-defined physicochemical meanings (Abraham and Acree, 2016). The model is shown as Eq.…”

Section: Introductionmentioning

confidence: 99%

Interpretation of toxicological activity of ionic liquids to acetylcholinesterase inhibition via in silico modelling

Cho

Yun

2016

Chemosphere

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In Silico Acute Aquatic Hazard Assessment and Prioritization Using a Grouped Target Site Model: A Case Study of Organic Substances Reported in Permian Basin Hydraulic Fracturing Operations

Boone,

Di Toro,

Davis

et al. 2024

Enviro Toxic and Chemistry

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Hydraulic fracturing (HF) is commonly used to enhance onshore recovery of oil and gas during production. This process involves the use of a variety of chemicals to support the physical extraction of oil and gas, maintain appropriate conditions downhole (e.g., redox conditions, pH), and limit microbial growth. The diversity of chemicals used in HF presents a significant challenge for risk assessment. The objective of the present study is to establish a transparent, reproducible procedure for estimating 5th percentile acute aquatic hazard concentrations (e.g., acute hazard concentration 5th percentiles [HC5s]) for these substances and validating against existing toxicity data. A simplified, grouped target site model (gTSM) was developed using a database (n = 1696) of diverse compounds with known mode of action (MoA) information. Statistical significance testing was employed to reduce model complexity by combining 11 discrete MoAs into three general hazard groups. The new model was trained and validated using an 80:20 allocation of the experimental database. The gTSM predicts toxicity using a combination of target site water partition coefficients and hazard group‐based critical target site concentrations. Model performance was comparable to the original TSM using 40% fewer parameters. Model predictions were judged to be sufficiently reliable and the gTSM was further used to prioritize a subset of reported Permian Basin HF substances for risk evaluation. The gTSM was applied to predict hazard groups, species acute toxicity, and acute HC5s for 186 organic compounds (neutral and ionic). Toxicity predictions and acute HC5 estimates were validated against measured acute toxicity data compiled for HF substances. This case study supports the gTSM as an efficient, cost‐effective computational tool for rapid aquatic hazard assessment of diverse organic chemicals. Environ Toxicol Chem 2024;00:1–12. © 2024 ExxonMobil Petroleum and Chemical BV. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC.

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Descriptors for ions and ion-pairs for use in linear free energy relationships

Cited by 62 publications

References 100 publications

An equation for the prediction of human skin permeability of neutral molecules, ions and ionic species

An equation for the prediction of human skin permeability of neutral molecules, ions and ionic species

Interpretation of toxicological activity of ionic liquids to acetylcholinesterase inhibition via in silico modelling

In Silico Acute Aquatic Hazard Assessment and Prioritization Using a Grouped Target Site Model: A Case Study of Organic Substances Reported in Permian Basin Hydraulic Fracturing Operations

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