Two-electron redox chemistry of p -nitro- and p -cyanobenzene diazohydroxides
The electrochemistry of aryl diazonium salts is usually dominated by one-electron reduction, loss of dinitrogen, and the grafting of aryl radicals onto the electrode. In contrast, -nitro- and -cyanobenzene diazonium salts dissolved in mixed aqueous-acetonitrile solvents showed diffusion-limited, qua...
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| Veröffentlicht in: | RSC advances 2018-12, Vol.8 (73), p.41762-41766 |
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| container_issue | 73 |
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| container_title | RSC advances |
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| creator | McEvoy, James P Pham, Nhan V Le, Hong T Fernandez, Micah M Farmer, Ryan P Mahapatro, Surendra N |
| description | The electrochemistry of aryl diazonium salts is usually dominated by one-electron reduction, loss of dinitrogen, and the grafting of aryl radicals onto the electrode. In contrast,
-nitro- and
-cyanobenzene diazonium salts dissolved in mixed aqueous-acetonitrile solvents showed diffusion-limited, quasi-reversible, two-electron cyclic voltammetry. Voltammetric pH-dependence and spectrophotometric kinetic studies suggest that the basicity and low polarity of the aqueous solvent mixture has revealed the biologically-significant interconversion of diazohydroxide and diazene. |
| doi_str_mv | 10.1039/c8ra05948a |
| format | Article |
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-nitro- and
-cyanobenzene diazonium salts dissolved in mixed aqueous-acetonitrile solvents showed diffusion-limited, quasi-reversible, two-electron cyclic voltammetry. Voltammetric pH-dependence and spectrophotometric kinetic studies suggest that the basicity and low polarity of the aqueous solvent mixture has revealed the biologically-significant interconversion of diazohydroxide and diazene.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c8ra05948a</identifier><identifier>PMID: 35558800</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Acetonitrile ; Aromatic compounds ; Basicity ; Chemistry ; Dependence ; Electrochemistry ; Electrons ; Organic chemistry ; Polarity ; Solvents ; Spectrophotometry ; Voltammetry</subject><ispartof>RSC advances, 2018-12, Vol.8 (73), p.41762-41766</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2018</rights><rights>This journal is © The Royal Society of Chemistry 2018 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c356t-bf80dd96e87aab91b66ce1899145102e238d97d76ab26e38706d2c1d34a8732c3</cites><orcidid>0000-0003-0542-3881 ; 0000000305423881</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092087/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092087/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35558800$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1485705$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>McEvoy, James P</creatorcontrib><creatorcontrib>Pham, Nhan V</creatorcontrib><creatorcontrib>Le, Hong T</creatorcontrib><creatorcontrib>Fernandez, Micah M</creatorcontrib><creatorcontrib>Farmer, Ryan P</creatorcontrib><creatorcontrib>Mahapatro, Surendra N</creatorcontrib><title>Two-electron redox chemistry of p -nitro- and p -cyanobenzene diazohydroxides</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>The electrochemistry of aryl diazonium salts is usually dominated by one-electron reduction, loss of dinitrogen, and the grafting of aryl radicals onto the electrode. In contrast,
-nitro- and
-cyanobenzene diazonium salts dissolved in mixed aqueous-acetonitrile solvents showed diffusion-limited, quasi-reversible, two-electron cyclic voltammetry. Voltammetric pH-dependence and spectrophotometric kinetic studies suggest that the basicity and low polarity of the aqueous solvent mixture has revealed the biologically-significant interconversion of diazohydroxide and diazene.</description><subject>Acetonitrile</subject><subject>Aromatic compounds</subject><subject>Basicity</subject><subject>Chemistry</subject><subject>Dependence</subject><subject>Electrochemistry</subject><subject>Electrons</subject><subject>Organic chemistry</subject><subject>Polarity</subject><subject>Solvents</subject><subject>Spectrophotometry</subject><subject>Voltammetry</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkV9rHCEUxaU0NGGTl36AMrQvpTDJVUdHXwLL0j-BlEJIn8XRu13DrG50ts3m09d005DWl6vcH-d6zyHkNYVTClyfOZUtCN0p-4IcMehky0Dql8_uh-SklBuoRwrKJH1FDrkQQimAI_L1-ldqcUQ35RSbjD7dNW6F61CmvGvSstk0bQy12TY2-oeX29mYBoz3GLHxwd6n1c7ndBc8lmNysLRjwZPHOiPfP328XnxpL799vljML1vHhZzaYanAey1R9dYOmg5SOqRKa9oJCgwZV173vpd2YBK56kF65qjnnVU9Z47PyPled7Md1ugdxinb0WxyWNu8M8kG828nhpX5kX4aDZpB1ZiRt3uBVKZgigsTupVLMVYjDO2U6EFU6P3jlJxut1gmU21xOI42YtoWw6TsFPRa6Yq--w-9SdscqweGUaE6DpJBpT7sKZdTKRmXTz-mYB7SNAt1Nf-T5rzCb57v-IT-zY7_Bs3cmW4</recordid><startdate>20181213</startdate><enddate>20181213</enddate><creator>McEvoy, James P</creator><creator>Pham, Nhan V</creator><creator>Le, Hong T</creator><creator>Fernandez, Micah M</creator><creator>Farmer, Ryan P</creator><creator>Mahapatro, Surendra N</creator><general>Royal Society of Chemistry</general><general>Royal Society of Chemistry (RSC)</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>OTOTI</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-0542-3881</orcidid><orcidid>https://orcid.org/0000000305423881</orcidid></search><sort><creationdate>20181213</creationdate><title>Two-electron redox chemistry of p -nitro- and p -cyanobenzene diazohydroxides</title><author>McEvoy, James P ; Pham, Nhan V ; Le, Hong T ; Fernandez, Micah M ; Farmer, Ryan P ; Mahapatro, Surendra N</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-bf80dd96e87aab91b66ce1899145102e238d97d76ab26e38706d2c1d34a8732c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetonitrile</topic><topic>Aromatic compounds</topic><topic>Basicity</topic><topic>Chemistry</topic><topic>Dependence</topic><topic>Electrochemistry</topic><topic>Electrons</topic><topic>Organic chemistry</topic><topic>Polarity</topic><topic>Solvents</topic><topic>Spectrophotometry</topic><topic>Voltammetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McEvoy, James P</creatorcontrib><creatorcontrib>Pham, Nhan V</creatorcontrib><creatorcontrib>Le, Hong T</creatorcontrib><creatorcontrib>Fernandez, Micah M</creatorcontrib><creatorcontrib>Farmer, Ryan P</creatorcontrib><creatorcontrib>Mahapatro, Surendra N</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McEvoy, James P</au><au>Pham, Nhan V</au><au>Le, Hong T</au><au>Fernandez, Micah M</au><au>Farmer, Ryan P</au><au>Mahapatro, Surendra N</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two-electron redox chemistry of p -nitro- and p -cyanobenzene diazohydroxides</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2018-12-13</date><risdate>2018</risdate><volume>8</volume><issue>73</issue><spage>41762</spage><epage>41766</epage><pages>41762-41766</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The electrochemistry of aryl diazonium salts is usually dominated by one-electron reduction, loss of dinitrogen, and the grafting of aryl radicals onto the electrode. In contrast,
-nitro- and
-cyanobenzene diazonium salts dissolved in mixed aqueous-acetonitrile solvents showed diffusion-limited, quasi-reversible, two-electron cyclic voltammetry. Voltammetric pH-dependence and spectrophotometric kinetic studies suggest that the basicity and low polarity of the aqueous solvent mixture has revealed the biologically-significant interconversion of diazohydroxide and diazene.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35558800</pmid><doi>10.1039/c8ra05948a</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-0542-3881</orcidid><orcidid>https://orcid.org/0000000305423881</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Acetonitrile Aromatic compounds Basicity Chemistry Dependence Electrochemistry Electrons Organic chemistry Polarity Solvents Spectrophotometry Voltammetry |
| title | Two-electron redox chemistry of p -nitro- and p -cyanobenzene diazohydroxides |
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