Quantitative structure–activity relationship for the partition coefficient of hydrophobic compounds between silicone oil and air

Quantitative structure–activity relationship for the partition coefficient of hydrophobic... The silicon oil-air partition coefficients (K SiO/A) of hydrophobic compounds are vital parameters for applying silicone oil as non-aqueous-phase liquid in partitioning bioreactors. Due to the limited number of K SiO/A values determined by experiment for hydrophobic compounds, there is an urgent need to model the K SiO/A values for unknown chemicals. In the present study, we developed a universal quantitative structure–activity relationship (QSAR) model using a sequential approach with macro-constitutional and micromolecular descriptors for silicone oil-air partition coefficients (K SiO/A) of hydrophobic compounds with large structural variance. The geometry optimization and vibrational frequencies of each chemical were calculated using the hybrid density functional theory at the B3LYP/6-311G** level. Several quantum chemical parameters that reflect various intermolecular interactions as well as hydrophobicity were selected to develop QSAR model. The result indicates that a regression model derived from logK SiO/A, the number of non-hydrogen atoms (#nonHatoms) and energy gap of E LUMO and E HOMO (E LUMO–E HOMO) could explain the partitioning mechanism of hydrophobic compounds between silicone oil and air. The correlation coefficient R 2 of the model is 0.922, and the internal and external validation coefficient, Q 2 LOO and Q 2 ext , are 0.91 and 0.89 respectively, implying that the model has satisfactory goodness-of-fit, robustness, and predictive ability and thus provides a robust predictive tool to estimate the logK SiO/A values for chemicals in application domain. The applicability domain of the model was visualized by the Williams plot. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Environmental Science and Pollution Research Springer Journals

Quantitative structure–activity relationship for the partition coefficient of hydrophobic compounds between silicone oil and air

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Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer-Verlag GmbH Germany, part of Springer Nature
Subject
Environment; Environment, general; Environmental Chemistry; Ecotoxicology; Environmental Health; Atmospheric Protection/Air Quality Control/Air Pollution; Waste Water Technology / Water Pollution Control / Water Management / Aquatic Pollution
ISSN
0944-1344
eISSN
1614-7499
D.O.I.
10.1007/s11356-018-1705-z
Publisher site
See Article on Publisher Site

Abstract

The silicon oil-air partition coefficients (K SiO/A) of hydrophobic compounds are vital parameters for applying silicone oil as non-aqueous-phase liquid in partitioning bioreactors. Due to the limited number of K SiO/A values determined by experiment for hydrophobic compounds, there is an urgent need to model the K SiO/A values for unknown chemicals. In the present study, we developed a universal quantitative structure–activity relationship (QSAR) model using a sequential approach with macro-constitutional and micromolecular descriptors for silicone oil-air partition coefficients (K SiO/A) of hydrophobic compounds with large structural variance. The geometry optimization and vibrational frequencies of each chemical were calculated using the hybrid density functional theory at the B3LYP/6-311G** level. Several quantum chemical parameters that reflect various intermolecular interactions as well as hydrophobicity were selected to develop QSAR model. The result indicates that a regression model derived from logK SiO/A, the number of non-hydrogen atoms (#nonHatoms) and energy gap of E LUMO and E HOMO (E LUMO–E HOMO) could explain the partitioning mechanism of hydrophobic compounds between silicone oil and air. The correlation coefficient R 2 of the model is 0.922, and the internal and external validation coefficient, Q 2 LOO and Q 2 ext , are 0.91 and 0.89 respectively, implying that the model has satisfactory goodness-of-fit, robustness, and predictive ability and thus provides a robust predictive tool to estimate the logK SiO/A values for chemicals in application domain. The applicability domain of the model was visualized by the Williams plot.

Journal

Environmental Science and Pollution Research – Springer Journals

Published: Mar 25, 2018

References

  • Gaseous hexane biodegradation by Fusarium solani in two liquid phase packed-bed and stirred-tank bioreactors
    Arriaga, S; Muñoz, R; Hernández, S; Guieysse, B; Revah, S
  • Quantitative structure-property relationship studies on n-octanol/water partitioning coefficients of PCDD/Fs
    Chen, J; Quan, X; Zhao, Y; Yan, YYF
  • Quantitative structure-property relationships for octanol-air partition coefficients of polychlorinated biphenyls
    Chen, J; Xue, X; Schramm, KW; Quan, X; Yang, F; Kettrup, A
  • Biological waste air treatment in biotrickling filters
    Cox, HH; Deshusses, MA
  • Two-phase partitioning bioreactors: a new technology platform for destroying xenobiotics
    Daugulis, AJ
  • How not to develop a quantitative structure-activity or structure-property relationship (QSAR/QSPR)
    Dearden, JC; Cronin, MTD; Kaiser, KLE
  • Determination of partition coefficients of three volatile organic compounds (dimethylsulphide, dimethyldisulphide and toluene) in water/silicone oil mixtures
    Dumont, E; Darracq, G; Couvert, A; Couriol, C; Amrane, A; Thomas, D; Andrès, Y; le Cloirec, P
  • Volumetric mass transfer coefficients characterising VOC absorption in water/silicone oil mixtures
    Dumont, E; Darracq, G; Couvert, A; Couriol, C; Amrane, A; Thomas, D; Andrès, Y; le Cloirec, P
  • Using theoretical descriptors in quantitative structure activity relationships: some physicochemical properties
    Famini, GR; Penski, CA; Wilson, L
  • Study on amphipathic modification and QSAR of volatile turpentine analogues as value-added botanical fungicides against crop-threatening pathogenic fungi
    Gao, Y; Tian, X; Li, J; Shang, S; Song, Z; Shen, M
  • Biotechnology: a highly efficient tool for the current environmental challenges
    García-Galán, MJ; Uggetti, E; Garfi, M; Olguín, EJ; García, J; Puigagut, J
  • Microbial degradation of phenanthrene and pyrene in a two-liquid phase-partitioning bioreactor
    Guieysse, B; Mattiasson, CB
  • Structure-activity analysis of harmful algae inhibition by congeneric compounds: case studies of fatty acids and thiazolidinediones
    Huang, H; Xiao, X; Shi, J; Chen, Y
  • QSAR applicabilty domain estimation by projection of the training set descriptor space: a review
    Jaworska, J; Nikolova, N; Aldenberg, T
  • Quantum-chemical descriptors in QSAR/QSPR studies
    Karelson, M; Lobanov, VS; Katritzky, AR
  • Review of mass transfer aspects for biological gas treatment
    Kraakman, NJR; Rocha-Rios, J; Loosdrecht, MCM
  • Removal of polycyclic aromatic hydrocarbons from contaminated soil in a two-phase partitioning bioreactor
    Lee, JY; Kwon, TS; Lee, YC
  • Field determination and QSPR prediction of equilibrium-status soil/vegetation partition coefficient of PCDD/Fs
    Li, L; Wang, Q; Qiu, X; Dong, Y; Jia, S; Hu, J
  • QSAR studies of bioconcentration factors of polychlorinated biphenyls (PCBs) using DFT, PCS and CoMFA
    Liu, H; Liu, H; Sun, P; Wang, Z
  • Development of TLSER model and QSAR model for predicting partition coefficients of hydrophobic organic chemicals between low density polyethylene film and water
    Liu, H; Wei, M; Yang, X; Yin, C; He, X
  • Combined removal of a BTEX, TCE, and cis-DCE mixture using Pseudomonas sp. immobilized on scrap tyres
    Lu, Q; Toledo, RA; Xie, F; Li, J; Shim, H
  • Mechanistic insight into reactivity of sulfate radical with aromatic contaminants through single-electron transfer pathway
    Luo, S; Wei, Z; Dionysiou, DD; Spinney, R; Hu, WP; Chai, L; Yang, Z; Ye, T; Xiao, R
  • A novel model to predict gas–phase hydroxyl radical oxidation kinetics of polychlorinated compounds
    Luo, S; Wei, Z; Spinney, R; Yang, Z; Chai, L; Xiao, R
  • Quantitative structure–activity relationships for reactivities of sulfate and hydroxyl radicals with aromatic contaminants through single–electron transfer pathway
    Luo, S; Wei, Z; Spinney, R; Villamena, FA; Dionysiou, DD; Chen, D; Tang, CJ; Chai, L; Xiao, R
  • UV direct photolysis of sulfamethoxazole and ibuprofen: an experimental and modelling study
    Luo, S; Wei, Z; Spinney, R; Zhang, Z; Dionysiou, DD; Gao, L; Chai, L; Wang, D; Xiao, R
  • Development and evaluation of predictive model for bovine serum albumin-water partition coefficients of neutral organic chemicals
    Ma, G; Yuan, Q; Yu, H; Lin, H; Chen, J; Hong, H
  • Oxygen mass transfer and shear stress effects on Pseudomonas putida BCRC 14365 growth to improve bioreactor design and performance
    Moradkhani, H; Izadkhah, MS; Anarjan, N; Abdi, A
  • Biorefinery
    Ohara, H
  • Assessment of methane biodegradation kinetics in two-phase partitioning bioreactors by pulse respirometry
    Ordaz, A; López, JC; Figueroa-González, I; Muñoz, R; Quijano, G
  • Determination and correlation of the partition coefficients of 48 volatile organic and environmentally relevant compounds between air and silicone oil
    Patel, MJ; Popat, SC; Deshusses, MA
  • Environmental biotechnology and engineering: crucial tools for improving and caring for the environment and the quality of life of modern societies
    Poggi-Varaldo, HM; Devault, DA; Macarie, H; Sastre-Conde, I
  • Simultaneous biodegradation of volatile and toxic contaminant mixtures by solid-liquid two-phase partitioning bioreactors
    Poleo, EE; Daugulis, AJ
  • Enhanced styrene removal in a two-phase partitioning bioreactor operated as a biotrickling filter: towards full-scale applications
    San-Valero, P; Gabaldón, C; Penya-roja, JM; Quijano, G
  • Biotrickling filter modeling for styrene abatement. Part 2: simulating a two-phase partitioning bioreactor
    San-Valero, P; Dorado, AD; Quijano, G; Álvarez-Hornos, FJ; Gabaldón, C
  • QSAR models for removal rates of organic pollutants adsorbed by in situ formed manganese dioxide under acid condition
    Su, P; Zhu, H; Shen, Z
  • QSAR models for oxidation of organic micropollutants in water based on ozone and hydroxyl radical rate constants and their chemical classification
    Sudhakaran, S; Amy, GL
  • A new combined green method for 2-Chlorophenol removal using cross-linked Brassica rapa peroxidase in silicone oil
    Tandjaoui, N; Abouseoud, M; Couvert, A; Amrane, A; Tassist, A
  • Application of quantum chemical descriptor in quantitative structure activity and structure property relationship
    Thanikaivelan, P; Subramanian, V; Rao, JR; Nair, BU
  • The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models
    Tropsha, A; Gramatica, P; Gombar, V
  • SIFT-MS analysis of the removal of dimethyl sulphide, n-hexane and toluene from waste air by a two phase partitioning bioreactor
    Volckaert, D; Ebude, DEL; Langenhove, H
  • Structural determination of paraffin boiling points
    Wiener, H
  • Quantitative structure-activity relationship (QSAR) for the oxidation of trace organic contaminants by sulfate radical
    Xiao, R; Ye, T; Wei, Z; Luo, S; Yang, Z; Spinney, R
  • Mechanistic insight into degradation of endocrine disrupting chemical by hydroxyl radical: an experimental and theoretical approach
    Xiao, R; Gao, L; Wei, Z; Spinney, R; Luo, S; Wang, D; Dionysiou, DD; Tang, C–J; Yang, W
  • Experimental and QSPR study of sorption properties of polychlorinated diphenyl sulfides (PCDPSs) in Yangtze River plain soil
    Yang, F; Qu, R; Wang, M; Tang, Y; Feng, M; Wang, Z
  • Rate constants of hydroxyl radical oxidation of polychlorinated biphenyls in the gas phase: a single− descriptor based QSAR and DFT study
    Yang, Z; Luo, S; Wei, Z; Ye, T; Spinney, R; Chen, D; Xiao, R
  • Comparison of the reactivity of ibuprofen with sulfate and hydroxyl radicals: an experimental and theoretical study
    Yang, Z; Su, R; Luo, S; Spinney, R; Cai, M; Xiao, R; Wei, Z
  • Chemical structure-based predictive model for the oxidation of trace organic contaminants by sulfate radical
    Ye, T; Wei, Z; Spinney, R; Tang, CJ; Luo, S; Xiao, R; Dionysiou, DD
  • Quantitative structure–activity relationship for the apparent rate constants of aromatic contaminants oxidized by ferrate (VI)
    Ye, T; Wei, Z; Spinney, R; Dionysiou, DD; Luo, S; Chai, L; Yang, Z; Xiao, R

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