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Predicting Sorbent-Air Partition Coefficients for Terpenoids at Multiple Temperatures.

ABSTRACT: Partition coefficients describe the relative concentration of a chemical equilibrated between two phases. In the design of air samplers, the sorbent-air partition coefficient is a critical parameter, as is the ability to extrapolate or predict partitioning at a variety of temperatures. Our specific interest is the partitioning of plant-derived terpenes (hydrocarbons formed from isoprene building blocks) and terpenoids (with oxygen-containing functional groups) in polydimethylsiloxane (PDMS) sorbents. To predict KPDMS/AIR as a function of temperature for compounds containing carbon, hydrogen, and oxygen, we developed a group contribution model that explicitly incorporates the van't Hoff equation. For the 360 training compounds, predicted KPDMS/AIR values strongly correlate (R2 > 0.987) with KPDMS/AIR values measured at temperatures from 60 °C to 200 °C. To validate the model with available literature data, we compared predictions for 50 additional C10 compounds, including 6 terpenes and 22 terpenoids, with KPDMS/AIR values measured at 100 °C and determined an average relative error of 3.1 %. We also compared predictions with KPDMS/AIR values measured at 25 °C. The modeling approach developed here is advantageous for properties with limited experimental values at a single temperature.

SUBMITTER: Jeerage KM

PROVIDER: S-EPMC8607369 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Predicting Sorbent-Air Partition Coefficients for Terpenoids at Multiple Temperatures.

Jeerage Kavita M KM Holland Elijah N EN

Industrial & engineering chemistry research 20200101 37

Partition coefficients describe the relative concentration of a chemical equilibrated between two phases. In the design of air samplers, the sorbent-air partition coefficient is a critical parameter, as is the ability to extrapolate or predict partitioning at a variety of temperatures. Our specific interest is the partitioning of plant-derived terpenes (hydrocarbons formed from isoprene building blocks) and terpenoids (with oxygen-containing functional groups) in polydimethylsiloxane (PDMS) sorb ...[more]

PMID: 34815620

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Project description:The partitioning of compounds between aqueous and other phases is important for predicting toxicity. Although thousands of octanol-water partition coefficients have been measured, these represent only a small fraction of the anthropogenic compounds present in the environment. The octanol phase is often taken to be a mimic of the inner parts of phospholipid membranes. However, the core of such membranes is typically more hydrophobic than octanol, and other partition coefficients with other compounds may give complementary information. Although a number of (cheap) empirical methods exist to compute octanol-water (log k OW) and hexadecane-water (log k HW) partition coefficients, it would be interesting to know whether physics-based models can predict these crucial values more accurately. Here, we have computed log k OW and log k HW for 133 compounds from seven different pollutant categories as well as a control group using the solvation model based on electronic density (SMD) protocol based on Hartree-Fock (HF) or density functional theory (DFT) and the COSMO-RS method. For comparison, XlogP3 (log k OW) values were retrieved from the PubChem database, and KowWin log k OW values were determined as well. For 24 of these compounds, log k OW was computed using potential of mean force (PMF) calculations based on classical molecular dynamics simulations. A comparison of the accuracy of the methods shows that COSMO-RS, KowWin, and XlogP3 all have a root-mean-square deviation (rmsd) from the experimental data of ≈0.4 log units, whereas the SMD protocol has an rmsd of 1.0 log units using HF and 0.9 using DFT. PMF calculations yield the poorest accuracy (rmsd = 1.1 log units). Thirty-six out of 133 calculations are for compounds without known log k OW, and for these, we provide what we consider a robust prediction, in the sense that there are few outliers, by averaging over the methods. The results supplied may be instrumental when developing new methods in computational ecotoxicity. The log k HW values are found to be strongly correlated to log k OW for most compounds.

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Predicting Sorbent-Air Partition Coefficients for Terpenoids at Multiple Temperatures.

Publications

Predicting Sorbent-Air Partition Coefficients for Terpenoids at Multiple Temperatures.

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