Quantitative structure-activity relationship for the photooxidation of aromatic micro-pollutants induced by graphene oxide in water

The photocatalytic degradation behavior of aromatic micro-pollutants (AMPs) exhibits complexity and uncertainty, which mainly depends on the properties of different substituents on benzene. And with similar catalytic reaction substrates, the reaction rate constant could reveal the influence of diffe...

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Veröffentlicht in:Chemosphere (Oxford) 2023-02, Vol.315, p.137781-137781, Article 137781
Hauptverfasser: Wang, Hao, Zou, Yongrong, Wang, Wenyu, Zhang, Yihui, Mailhot, Gilles, Li, Jinjun, Wu, Feng, Luo, Liting
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container_title Chemosphere (Oxford)
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creator Wang, Hao
Zou, Yongrong
Wang, Wenyu
Zhang, Yihui
Mailhot, Gilles
Li, Jinjun
Wu, Feng
Luo, Liting
description The photocatalytic degradation behavior of aromatic micro-pollutants (AMPs) exhibits complexity and uncertainty, which mainly depends on the properties of different substituents on benzene. And with similar catalytic reaction substrates, the reaction rate constant could reveal the influence of different characteristics of molecular structure in a specific system. Therefore, the photooxidation pseudo first-order kinetic rate constants (kobs) of 30 AMPs were experimentally determined in Photo-GO system. A quantitative structure-activity relationship (QSAR) model for predicting the photooxidation reaction of AMPs has been developed by stepwise multiple linear regression (MLR) method, based on the lg kobs and representative molecule descriptors (20 in total) including physicochemical, quantum chemical and electrostatic descriptors. Afterwards, Radj2, QLOO2, and Qext2 were calculated as 0.870, 0.841, and 0.732 respectively, which exhibited the excellent goodness-of-fit, robustness, and predictability of the QSAR model, indicating its great prediction ability for photooxidation behavior of AMPs. Meanwhile, during the photooxidation process of AMPs with GO, the model revealed that the one-electron oxidation potential (Eox), molecular dipole moment (μ), and number of hydrogen bond donors (#HD) were the most important molecular structural parameters, which showed that the single electron transfer pathway and adsorption were as the significant steps. Additionally, the Hammett correlation showed that photooxidation of AMPs in Photo-GO system is of typical electrophilic reactions, which demonstrated that the electron-donating substituents could promote the photooxidation of AMPs. The QSAR model was constructed and evaluated to perform the prediction of AMPs reaction kinetics, which provided a guidance for the study of the mechanism and selective oxidation of AOPs photooxidation system based on GO. [Display omitted] •Degradation of AMPs in Photo-GO system appears to be structure-dependent.•A QSAR model for AMPs oxidation in Photo-GO system was established.•AMPs with electron-donating substituents have higher reactivity of photooxidation.•The mechanisms of Photo-GO system were explained with QSAR model.
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And with similar catalytic reaction substrates, the reaction rate constant could reveal the influence of different characteristics of molecular structure in a specific system. Therefore, the photooxidation pseudo first-order kinetic rate constants (kobs) of 30 AMPs were experimentally determined in Photo-GO system. A quantitative structure-activity relationship (QSAR) model for predicting the photooxidation reaction of AMPs has been developed by stepwise multiple linear regression (MLR) method, based on the lg kobs and representative molecule descriptors (20 in total) including physicochemical, quantum chemical and electrostatic descriptors. Afterwards, Radj2, QLOO2, and Qext2 were calculated as 0.870, 0.841, and 0.732 respectively, which exhibited the excellent goodness-of-fit, robustness, and predictability of the QSAR model, indicating its great prediction ability for photooxidation behavior of AMPs. Meanwhile, during the photooxidation process of AMPs with GO, the model revealed that the one-electron oxidation potential (Eox), molecular dipole moment (μ), and number of hydrogen bond donors (#HD) were the most important molecular structural parameters, which showed that the single electron transfer pathway and adsorption were as the significant steps. Additionally, the Hammett correlation showed that photooxidation of AMPs in Photo-GO system is of typical electrophilic reactions, which demonstrated that the electron-donating substituents could promote the photooxidation of AMPs. The QSAR model was constructed and evaluated to perform the prediction of AMPs reaction kinetics, which provided a guidance for the study of the mechanism and selective oxidation of AOPs photooxidation system based on GO. [Display omitted] •Degradation of AMPs in Photo-GO system appears to be structure-dependent.•A QSAR model for AMPs oxidation in Photo-GO system was established.•AMPs with electron-donating substituents have higher reactivity of photooxidation.•The mechanisms of Photo-GO system were explained with QSAR model.</description><identifier>ISSN: 0045-6535</identifier><identifier>EISSN: 1879-1298</identifier><identifier>DOI: 10.1016/j.chemosphere.2023.137781</identifier><identifier>PMID: 36623604</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Aromatic micro-pollutants degradation ; Chemical Sciences ; Electrophilic reaction and selective oxidation ; Environmental Pollutants ; Graphite ; Hammett correlation ; Photo-GO system ; Quantitative Structure-Activity Relationship ; Water ; Water Pollutants, Chemical - analysis</subject><ispartof>Chemosphere (Oxford), 2023-02, Vol.315, p.137781-137781, Article 137781</ispartof><rights>2023 Elsevier Ltd</rights><rights>Copyright © 2023 Elsevier Ltd. 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Meanwhile, during the photooxidation process of AMPs with GO, the model revealed that the one-electron oxidation potential (Eox), molecular dipole moment (μ), and number of hydrogen bond donors (#HD) were the most important molecular structural parameters, which showed that the single electron transfer pathway and adsorption were as the significant steps. Additionally, the Hammett correlation showed that photooxidation of AMPs in Photo-GO system is of typical electrophilic reactions, which demonstrated that the electron-donating substituents could promote the photooxidation of AMPs. The QSAR model was constructed and evaluated to perform the prediction of AMPs reaction kinetics, which provided a guidance for the study of the mechanism and selective oxidation of AOPs photooxidation system based on GO. [Display omitted] •Degradation of AMPs in Photo-GO system appears to be structure-dependent.•A QSAR model for AMPs oxidation in Photo-GO system was established.•AMPs with electron-donating substituents have higher reactivity of photooxidation.•The mechanisms of Photo-GO system were explained with QSAR model.</description><subject>Aromatic micro-pollutants degradation</subject><subject>Chemical Sciences</subject><subject>Electrophilic reaction and selective oxidation</subject><subject>Environmental Pollutants</subject><subject>Graphite</subject><subject>Hammett correlation</subject><subject>Photo-GO system</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Water</subject><subject>Water Pollutants, Chemical - analysis</subject><issn>0045-6535</issn><issn>1879-1298</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNUUtv1DAQthAVXQp_AZkbHLK187CdY7XqA2klhARny5lMiFdJHGxnYc_8cbxNqTjii-X5HjOej5D3nG054-L6sIUeRxfmHj1uc5YXW15IqfgLsuFK1hnPa_WSbBgrq0xURXVJXodwYCyJq_oVuSyEyAvByg35_WUxU7TRRHtEGqJfIC4eMwOpYOOJehwS5qbQ25l2ztPYI517F537ZdtHiLqOGu_G9AA6WvAum90wLDE5B2qndgFsaXOi371JI09Iz1JMCP1pIvo35KIzQ8C3T_cV-XZ3-3X3kO0_33_a3ewzKDmPGTRtC10DUCtRQSEUV2jKEpsSWsNZ06qyhqYAWfMcZMI7WefAjOyEUWVa0hX5uPr2ZtCzt6PxJ-2M1Q83e32usbJgUjJ25In7YeXO3v1YMEQ92gA4DGZCtwSdS1Gko5RI1Hqlpo-H4LF79uZMn_PSB_1PXvqcl17zStp3T22WZsT2Wfk3oETYrQRMizla9DqAxSkt1HqEqFtn_6PNH_11sJU</recordid><startdate>20230201</startdate><enddate>20230201</enddate><creator>Wang, Hao</creator><creator>Zou, Yongrong</creator><creator>Wang, Wenyu</creator><creator>Zhang, Yihui</creator><creator>Mailhot, Gilles</creator><creator>Li, Jinjun</creator><creator>Wu, Feng</creator><creator>Luo, Liting</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-8179-8880</orcidid><orcidid>https://orcid.org/0000-0003-2846-5494</orcidid><orcidid>https://orcid.org/0000-0002-6963-5173</orcidid><orcidid>https://orcid.org/0000-0003-4008-9022</orcidid></search><sort><creationdate>20230201</creationdate><title>Quantitative structure-activity relationship for the photooxidation of aromatic micro-pollutants induced by graphene oxide in water</title><author>Wang, Hao ; 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And with similar catalytic reaction substrates, the reaction rate constant could reveal the influence of different characteristics of molecular structure in a specific system. Therefore, the photooxidation pseudo first-order kinetic rate constants (kobs) of 30 AMPs were experimentally determined in Photo-GO system. A quantitative structure-activity relationship (QSAR) model for predicting the photooxidation reaction of AMPs has been developed by stepwise multiple linear regression (MLR) method, based on the lg kobs and representative molecule descriptors (20 in total) including physicochemical, quantum chemical and electrostatic descriptors. Afterwards, Radj2, QLOO2, and Qext2 were calculated as 0.870, 0.841, and 0.732 respectively, which exhibited the excellent goodness-of-fit, robustness, and predictability of the QSAR model, indicating its great prediction ability for photooxidation behavior of AMPs. Meanwhile, during the photooxidation process of AMPs with GO, the model revealed that the one-electron oxidation potential (Eox), molecular dipole moment (μ), and number of hydrogen bond donors (#HD) were the most important molecular structural parameters, which showed that the single electron transfer pathway and adsorption were as the significant steps. Additionally, the Hammett correlation showed that photooxidation of AMPs in Photo-GO system is of typical electrophilic reactions, which demonstrated that the electron-donating substituents could promote the photooxidation of AMPs. The QSAR model was constructed and evaluated to perform the prediction of AMPs reaction kinetics, which provided a guidance for the study of the mechanism and selective oxidation of AOPs photooxidation system based on GO. [Display omitted] •Degradation of AMPs in Photo-GO system appears to be structure-dependent.•A QSAR model for AMPs oxidation in Photo-GO system was established.•AMPs with electron-donating substituents have higher reactivity of photooxidation.•The mechanisms of Photo-GO system were explained with QSAR model.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>36623604</pmid><doi>10.1016/j.chemosphere.2023.137781</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-8179-8880</orcidid><orcidid>https://orcid.org/0000-0003-2846-5494</orcidid><orcidid>https://orcid.org/0000-0002-6963-5173</orcidid><orcidid>https://orcid.org/0000-0003-4008-9022</orcidid></addata></record>
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subjects Aromatic micro-pollutants degradation
Chemical Sciences
Electrophilic reaction and selective oxidation
Environmental Pollutants
Graphite
Hammett correlation
Photo-GO system
Quantitative Structure-Activity Relationship
Water
Water Pollutants, Chemical - analysis
title Quantitative structure-activity relationship for the photooxidation of aromatic micro-pollutants induced by graphene oxide in water
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