The autoprotonation in reduction mechanism of pesticide ioxynil

The reduction mechanism of ioxynil (3,5-diiodo-4-hydroxy-benzonitrile) was studied in dimethylsulfoxide using the electrochemical methods (tast polarography, cyclic voltammetry and controlled potential electrolysis) combined with GC/MS identification of products. The reduction is accompanied by the...

Full description

Saved in:
Bibliographic Details
Published in:Electrochimica acta 2010-11, Vol.55 (27), p.8336-8340
Main Authors: Sokolová, Romana, Hromadová, Magdaléna, Ludvík, Jiří, Pospíšil, Lubomír, Giannarelli, Stefania
Format: Article
Language:English
Subjects:
Autoprotonation
Chemistry
Cleavage
Electrochemistry
Electrolysis
Exact sciences and technology
General and physical chemistry
Iodides
Kinetics and mechanism of reactions
Organic halides
Pesticides
Polarography
Reduction
Reduction (electrolytic)
Solvents
Uptakes
Voltammetry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23
cites cdi_FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23
container_end_page 8340
container_issue 27
container_start_page 8336
container_title Electrochimica acta
container_volume 55
creator Sokolová, Romana
Hromadová, Magdaléna
Ludvík, Jiří
Pospíšil, Lubomír
Giannarelli, Stefania
description The reduction mechanism of ioxynil (3,5-diiodo-4-hydroxy-benzonitrile) was studied in dimethylsulfoxide using the electrochemical methods (tast polarography, cyclic voltammetry and controlled potential electrolysis) combined with GC/MS identification of products. The reduction is accompanied by the cleavage of iodide yielding 3-iodo-4-hydroxybenzonitrile. Surprisingly, this process requires only one electron for the exhaustive electrolysis of the starting compound. We showed that the apparent one electron reduction observed in the aprotic solvent is due to the autoprotonation by another molecule of ioxynil. The overall one electron reduction (uptake of two electrons per two molecules of ioxynil) is changed in the presence of a strong proton donor to a two electron process per one molecule.
doi_str_mv 10.1016/j.electacta.2010.01.094
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_822523311</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0013468610001830</els_id><sourcerecordid>822523311</sourcerecordid><originalsourceid>FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23</originalsourceid><addsrcrecordid>eNqFUEtLAzEQDqJgrf4G9yKedp0ku9n0JKX4goKXeg7TPGjKdlOTrdh_b2qLV2FgmOF7zHyE3FKoKFDxsK5sZ_WAuSoGeQu0gkl9RkZUtrzkspmckxEA5WUtpLgkVymtAaAVLYzI42JlC9wNYRvDEHocfOgL3xfRmp3-HTZWr7D3aVMEV2xtGrz2xhY-fO97312TC4ddsjenPiYfz0-L2Ws5f395m03npeZtO5RLIxozMUIYZ5YNOrpE2bQInDYNotDcgeOihrZmhkkHyKRERtGYvNaa8TG5P-rmOz93-Qq18UnbrsPehl1SkrGGcU5pRrZHpI4hpWid2ka_wbhXFNQhMbVWf4mpQ2IKqMqJZebdyQOTxs5F7LVPf3TGa1Y3UmTc9Iiz-eEvb6NK2tteW-Nj1lUm-H-9fgAZ2oa2</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>822523311</pqid></control><display><type>article</type><title>The autoprotonation in reduction mechanism of pesticide ioxynil</title><source>ScienceDirect Freedom Collection 2022-2024</source><creator>Sokolová, Romana ; Hromadová, Magdaléna ; Ludvík, Jiří ; Pospíšil, Lubomír ; Giannarelli, Stefania</creator><creatorcontrib>Sokolová, Romana ; Hromadová, Magdaléna ; Ludvík, Jiří ; Pospíšil, Lubomír ; Giannarelli, Stefania</creatorcontrib><description>The reduction mechanism of ioxynil (3,5-diiodo-4-hydroxy-benzonitrile) was studied in dimethylsulfoxide using the electrochemical methods (tast polarography, cyclic voltammetry and controlled potential electrolysis) combined with GC/MS identification of products. The reduction is accompanied by the cleavage of iodide yielding 3-iodo-4-hydroxybenzonitrile. Surprisingly, this process requires only one electron for the exhaustive electrolysis of the starting compound. We showed that the apparent one electron reduction observed in the aprotic solvent is due to the autoprotonation by another molecule of ioxynil. The overall one electron reduction (uptake of two electrons per two molecules of ioxynil) is changed in the presence of a strong proton donor to a two electron process per one molecule.</description><identifier>ISSN: 0013-4686</identifier><identifier>EISSN: 1873-3859</identifier><identifier>DOI: 10.1016/j.electacta.2010.01.094</identifier><identifier>CODEN: ELCAAV</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Autoprotonation ; Chemistry ; Cleavage ; Electrochemistry ; Electrolysis ; Exact sciences and technology ; General and physical chemistry ; Iodides ; Kinetics and mechanism of reactions ; Organic halides ; Pesticides ; Polarography ; Reduction ; Reduction (electrolytic) ; Solvents ; Uptakes ; Voltammetry</subject><ispartof>Electrochimica acta, 2010-11, Vol.55 (27), p.8336-8340</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23</citedby><cites>FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>309,310,314,780,784,789,790,23930,23931,25140,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=23424586$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Sokolová, Romana</creatorcontrib><creatorcontrib>Hromadová, Magdaléna</creatorcontrib><creatorcontrib>Ludvík, Jiří</creatorcontrib><creatorcontrib>Pospíšil, Lubomír</creatorcontrib><creatorcontrib>Giannarelli, Stefania</creatorcontrib><title>The autoprotonation in reduction mechanism of pesticide ioxynil</title><title>Electrochimica acta</title><description>The reduction mechanism of ioxynil (3,5-diiodo-4-hydroxy-benzonitrile) was studied in dimethylsulfoxide using the electrochemical methods (tast polarography, cyclic voltammetry and controlled potential electrolysis) combined with GC/MS identification of products. The reduction is accompanied by the cleavage of iodide yielding 3-iodo-4-hydroxybenzonitrile. Surprisingly, this process requires only one electron for the exhaustive electrolysis of the starting compound. We showed that the apparent one electron reduction observed in the aprotic solvent is due to the autoprotonation by another molecule of ioxynil. The overall one electron reduction (uptake of two electrons per two molecules of ioxynil) is changed in the presence of a strong proton donor to a two electron process per one molecule.</description><subject>Autoprotonation</subject><subject>Chemistry</subject><subject>Cleavage</subject><subject>Electrochemistry</subject><subject>Electrolysis</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Iodides</subject><subject>Kinetics and mechanism of reactions</subject><subject>Organic halides</subject><subject>Pesticides</subject><subject>Polarography</subject><subject>Reduction</subject><subject>Reduction (electrolytic)</subject><subject>Solvents</subject><subject>Uptakes</subject><subject>Voltammetry</subject><issn>0013-4686</issn><issn>1873-3859</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFUEtLAzEQDqJgrf4G9yKedp0ku9n0JKX4goKXeg7TPGjKdlOTrdh_b2qLV2FgmOF7zHyE3FKoKFDxsK5sZ_WAuSoGeQu0gkl9RkZUtrzkspmckxEA5WUtpLgkVymtAaAVLYzI42JlC9wNYRvDEHocfOgL3xfRmp3-HTZWr7D3aVMEV2xtGrz2xhY-fO97312TC4ddsjenPiYfz0-L2Ws5f395m03npeZtO5RLIxozMUIYZ5YNOrpE2bQInDYNotDcgeOihrZmhkkHyKRERtGYvNaa8TG5P-rmOz93-Qq18UnbrsPehl1SkrGGcU5pRrZHpI4hpWid2ka_wbhXFNQhMbVWf4mpQ2IKqMqJZebdyQOTxs5F7LVPf3TGa1Y3UmTc9Iiz-eEvb6NK2tteW-Nj1lUm-H-9fgAZ2oa2</recordid><startdate>20101130</startdate><enddate>20101130</enddate><creator>Sokolová, Romana</creator><creator>Hromadová, Magdaléna</creator><creator>Ludvík, Jiří</creator><creator>Pospíšil, Lubomír</creator><creator>Giannarelli, Stefania</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20101130</creationdate><title>The autoprotonation in reduction mechanism of pesticide ioxynil</title><author>Sokolová, Romana ; Hromadová, Magdaléna ; Ludvík, Jiří ; Pospíšil, Lubomír ; Giannarelli, Stefania</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Autoprotonation</topic><topic>Chemistry</topic><topic>Cleavage</topic><topic>Electrochemistry</topic><topic>Electrolysis</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Iodides</topic><topic>Kinetics and mechanism of reactions</topic><topic>Organic halides</topic><topic>Pesticides</topic><topic>Polarography</topic><topic>Reduction</topic><topic>Reduction (electrolytic)</topic><topic>Solvents</topic><topic>Uptakes</topic><topic>Voltammetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sokolová, Romana</creatorcontrib><creatorcontrib>Hromadová, Magdaléna</creatorcontrib><creatorcontrib>Ludvík, Jiří</creatorcontrib><creatorcontrib>Pospíšil, Lubomír</creatorcontrib><creatorcontrib>Giannarelli, Stefania</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Electrochimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sokolová, Romana</au><au>Hromadová, Magdaléna</au><au>Ludvík, Jiří</au><au>Pospíšil, Lubomír</au><au>Giannarelli, Stefania</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The autoprotonation in reduction mechanism of pesticide ioxynil</atitle><jtitle>Electrochimica acta</jtitle><date>2010-11-30</date><risdate>2010</risdate><volume>55</volume><issue>27</issue><spage>8336</spage><epage>8340</epage><pages>8336-8340</pages><issn>0013-4686</issn><eissn>1873-3859</eissn><coden>ELCAAV</coden><abstract>The reduction mechanism of ioxynil (3,5-diiodo-4-hydroxy-benzonitrile) was studied in dimethylsulfoxide using the electrochemical methods (tast polarography, cyclic voltammetry and controlled potential electrolysis) combined with GC/MS identification of products. The reduction is accompanied by the cleavage of iodide yielding 3-iodo-4-hydroxybenzonitrile. Surprisingly, this process requires only one electron for the exhaustive electrolysis of the starting compound. We showed that the apparent one electron reduction observed in the aprotic solvent is due to the autoprotonation by another molecule of ioxynil. The overall one electron reduction (uptake of two electrons per two molecules of ioxynil) is changed in the presence of a strong proton donor to a two electron process per one molecule.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.electacta.2010.01.094</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0013-4686
ispartof Electrochimica acta, 2010-11, Vol.55 (27), p.8336-8340
issn 0013-4686
1873-3859
language eng
recordid cdi_proquest_miscellaneous_822523311
source ScienceDirect Freedom Collection 2022-2024
subjects Autoprotonation
Chemistry
Cleavage
Electrochemistry
Electrolysis
Exact sciences and technology
General and physical chemistry
Iodides
Kinetics and mechanism of reactions
Organic halides
Pesticides
Polarography
Reduction
Reduction (electrolytic)
Solvents
Uptakes
Voltammetry
title The autoprotonation in reduction mechanism of pesticide ioxynil
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T03%3A19%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20autoprotonation%20in%20reduction%20mechanism%20of%20pesticide%20ioxynil&rft.jtitle=Electrochimica%20acta&rft.au=Sokolov%C3%A1,%20Romana&rft.date=2010-11-30&rft.volume=55&rft.issue=27&rft.spage=8336&rft.epage=8340&rft.pages=8336-8340&rft.issn=0013-4686&rft.eissn=1873-3859&rft.coden=ELCAAV&rft_id=info:doi/10.1016/j.electacta.2010.01.094&rft_dat=%3Cproquest_cross%3E822523311%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c377t-bd65d9d66dfdb5af1ba857a03155aa6c3f0f3640742d28f0a288a21addf36cc23%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=822523311&rft_id=info:pmid/&rfr_iscdi=true