Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism

Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism

The rates and products of dediazoniation of benzenediazonium tetrafluoroborate in 2,2,2‐trifluoroethanol (TFE)/water mixtures has been determined. The results are not consistent with a mechanism in which TFE and water enter the rate‐determining part of the reaction as nucleophiles. The influence of...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Helvetica chimica acta 1974-11, Vol.57 (7), p.2099-2105
Hauptverfasser: Burri, Peter, Wahl Jr, George H., Zollinger, Heinrich
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2105
container_issue 7
container_start_page 2099
container_title Helvetica chimica acta
container_volume 57
creator Burri, Peter
Wahl Jr, George H.
Zollinger, Heinrich
description The rates and products of dediazoniation of benzenediazonium tetrafluoroborate in 2,2,2‐trifluoroethanol (TFE)/water mixtures has been determined. The results are not consistent with a mechanism in which TFE and water enter the rate‐determining part of the reaction as nucleophiles. The influence of the solvent composition on product ratios and rates is explained as a solvent effect, the formation of a (solvated) aryl cation being the rate‐determining part of the reaction. The magnitude of the preexponential factor of the Arrhenius equation is consistent with this interpretation. Since the solvolysis of p ‐chlorobenzenediazonium tetrafluoroborate in TFE yields no detectable m‐products, an aryne‐like mechanism is excluded.
doi_str_mv 10.1002/hlca.19740570724
format Article
fullrecord <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_hlca_19740570724</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>HLCA19740570724</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3144-6911875c78ba92ff38b5446a1d1297278b01d2c3caffc3fa3faf703c373cb9f3</originalsourceid><addsrcrecordid>eNqFkN1OGzEQha0KpAbofS_9AN0wtnfX2Uq9iMJPIiKoVFS4sxzHLqbeNbK9JeGR-pR4CULtFRpLIx2fb2Z0EPpMYEwA6PGdU3JMGl5CxYHT8gMakYrSgta82kMjADIpgDS3H9FBjPcA0DTAR-jviV5b-eQ7K5P1XcTe4GnQncYnO7lv8WLQbYfnvvW_8pfvI_7hXT8AY_xdhoR_Lr4O0h_vtlG_mOmXXEUK1rjeB6_Tney8O36USQfc2k3qQzbKbo31Rrk-5lnDbokffNJdstJhGbb5jlarjNrYHqF9I13Un177Ibo-O72ezYvl1fliNl0WipGyLOqGkAmvFJ-sZEONYZNVVZa1JGtCG06zDGRNFVPSGMWMzM9wYIpxplaNYYcIdmNV8DEGbcRDsG2-RRAQQ9RiiFr8E3VGvu2QR-v09l2_mC9n0__5YsfbmPTmjZfht6g545W4uTwXF_yM1uVyLoA9AwTUlvU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Burri, Peter ; Wahl Jr, George H. ; Zollinger, Heinrich</creator><creatorcontrib>Burri, Peter ; Wahl Jr, George H. ; Zollinger, Heinrich</creatorcontrib><description>The rates and products of dediazoniation of benzenediazonium tetrafluoroborate in 2,2,2‐trifluoroethanol (TFE)/water mixtures has been determined. The results are not consistent with a mechanism in which TFE and water enter the rate‐determining part of the reaction as nucleophiles. The influence of the solvent composition on product ratios and rates is explained as a solvent effect, the formation of a (solvated) aryl cation being the rate‐determining part of the reaction. The magnitude of the preexponential factor of the Arrhenius equation is consistent with this interpretation. Since the solvolysis of p ‐chlorobenzenediazonium tetrafluoroborate in TFE yields no detectable m‐products, an aryne‐like mechanism is excluded.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.19740570724</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><ispartof>Helvetica chimica acta, 1974-11, Vol.57 (7), p.2099-2105</ispartof><rights>Copyright © 1974 Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3144-6911875c78ba92ff38b5446a1d1297278b01d2c3caffc3fa3faf703c373cb9f3</citedby><cites>FETCH-LOGICAL-c3144-6911875c78ba92ff38b5446a1d1297278b01d2c3caffc3fa3faf703c373cb9f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fhlca.19740570724$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.19740570724$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Burri, Peter</creatorcontrib><creatorcontrib>Wahl Jr, George H.</creatorcontrib><creatorcontrib>Zollinger, Heinrich</creatorcontrib><title>Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>The rates and products of dediazoniation of benzenediazonium tetrafluoroborate in 2,2,2‐trifluoroethanol (TFE)/water mixtures has been determined. The results are not consistent with a mechanism in which TFE and water enter the rate‐determining part of the reaction as nucleophiles. The influence of the solvent composition on product ratios and rates is explained as a solvent effect, the formation of a (solvated) aryl cation being the rate‐determining part of the reaction. The magnitude of the preexponential factor of the Arrhenius equation is consistent with this interpretation. Since the solvolysis of p ‐chlorobenzenediazonium tetrafluoroborate in TFE yields no detectable m‐products, an aryne‐like mechanism is excluded.</description><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1974</creationdate><recordtype>article</recordtype><recordid>eNqFkN1OGzEQha0KpAbofS_9AN0wtnfX2Uq9iMJPIiKoVFS4sxzHLqbeNbK9JeGR-pR4CULtFRpLIx2fb2Z0EPpMYEwA6PGdU3JMGl5CxYHT8gMakYrSgta82kMjADIpgDS3H9FBjPcA0DTAR-jviV5b-eQ7K5P1XcTe4GnQncYnO7lv8WLQbYfnvvW_8pfvI_7hXT8AY_xdhoR_Lr4O0h_vtlG_mOmXXEUK1rjeB6_Tney8O36USQfc2k3qQzbKbo31Rrk-5lnDbokffNJdstJhGbb5jlarjNrYHqF9I13Un177Ibo-O72ezYvl1fliNl0WipGyLOqGkAmvFJ-sZEONYZNVVZa1JGtCG06zDGRNFVPSGMWMzM9wYIpxplaNYYcIdmNV8DEGbcRDsG2-RRAQQ9RiiFr8E3VGvu2QR-v09l2_mC9n0__5YsfbmPTmjZfht6g545W4uTwXF_yM1uVyLoA9AwTUlvU</recordid><startdate>19741106</startdate><enddate>19741106</enddate><creator>Burri, Peter</creator><creator>Wahl Jr, George H.</creator><creator>Zollinger, Heinrich</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19741106</creationdate><title>Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism</title><author>Burri, Peter ; Wahl Jr, George H. ; Zollinger, Heinrich</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3144-6911875c78ba92ff38b5446a1d1297278b01d2c3caffc3fa3faf703c373cb9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1974</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Burri, Peter</creatorcontrib><creatorcontrib>Wahl Jr, George H.</creatorcontrib><creatorcontrib>Zollinger, Heinrich</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Burri, Peter</au><au>Wahl Jr, George H.</au><au>Zollinger, Heinrich</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>1974-11-06</date><risdate>1974</risdate><volume>57</volume><issue>7</issue><spage>2099</spage><epage>2105</epage><pages>2099-2105</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>The rates and products of dediazoniation of benzenediazonium tetrafluoroborate in 2,2,2‐trifluoroethanol (TFE)/water mixtures has been determined. The results are not consistent with a mechanism in which TFE and water enter the rate‐determining part of the reaction as nucleophiles. The influence of the solvent composition on product ratios and rates is explained as a solvent effect, the formation of a (solvated) aryl cation being the rate‐determining part of the reaction. The magnitude of the preexponential factor of the Arrhenius equation is consistent with this interpretation. Since the solvolysis of p ‐chlorobenzenediazonium tetrafluoroborate in TFE yields no detectable m‐products, an aryne‐like mechanism is excluded.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/hlca.19740570724</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0018-019X
ispartof Helvetica chimica acta, 1974-11, Vol.57 (7), p.2099-2105
issn 0018-019X
1522-2675
language eng
recordid cdi_crossref_primary_10_1002_hlca_19740570724
source Wiley Online Library Journals Frontfile Complete
title Dediazoniations of Arene Diazonium Ions in Homogeneous Solution. Part VI: Solvolyses in 2,2,2-trifluoroethanol/water mixtures and exclusion of a potential aryne mechanism
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T00%3A26%3A15IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Dediazoniations%20of%20Arene%20Diazonium%20Ions%20in%20Homogeneous%20Solution.%20Part%20VI:%20Solvolyses%20in%202,2,2-trifluoroethanol/water%20mixtures%20and%20exclusion%20of%20a%20potential%20aryne%20mechanism&rft.jtitle=Helvetica%20chimica%20acta&rft.au=Burri,%20Peter&rft.date=1974-11-06&rft.volume=57&rft.issue=7&rft.spage=2099&rft.epage=2105&rft.pages=2099-2105&rft.issn=0018-019X&rft.eissn=1522-2675&rft_id=info:doi/10.1002/hlca.19740570724&rft_dat=%3Cwiley_cross%3EHLCA19740570724%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true