Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols
Identifieur interne : 002287 ( Istex/Corpus ); précédent : 002286; suivant : 002288Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols
Auteurs : Paul Müller ; Jean-Claude PerlbergerSource :
- Helvetica Chimica Acta [ 0018-019X ] ; 1976-11-03.
English descriptors
- Teeft :
- Acetic acid, Acta, Alcohol oxidation, Amer, Chem, Chimica, Chromic acid oxidation, Column ffap, Correlation coefficient, Eliel, Energy diagram, Epimeric, Epimeric alcohols, Equilibrium constants, Fasc, Helvetica, Helvetica chimica acta, Isotope effect, Isotope effects, Lower limit, Oxidation rates, Rate constants, Regression line, Sicher, Sicher correlation, Sicher plot, Standard deviation, Strain difference, Tlie, Transition state, Transition states.
Abstract
The linear free energy relationship of Sicher for relative reactivity towards chromic acid oxidation (ΔΔG Ox≠) as a function of thermodynamic stability (ΔG eq0) has been reexamined with 23 pairs of epimeric alcohols. The plot of ΔG Ox≠ vs. ΔG eq0 has a slope of 0.8, a correlation coefficient of 0.97 and a standard deviation of 0.23 kcal/mol on ΔΔGOx Ox≠. The limitations of the relationship and the exceptions are discussed.
Url:
DOI: 10.1002/hlca.19760590706
Links to Exploration step
ISTEX:9500174825779537F2FFA54243096576AE8FAF71Le document en format XML
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Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title><author><name sortKey="Muller, Paul" sort="Muller, Paul" uniqKey="Muller P" first="Paul" last="Müller">Paul Müller</name><affiliation><mods:affiliation>Département de Chimie Organique, Université de Genève, 1211 Genève 4</mods:affiliation></affiliation></author><author><name sortKey="Perlberger, Jean Laude" sort="Perlberger, Jean Laude" uniqKey="Perlberger J" first="Jean-Claude" last="Perlberger">Jean-Claude Perlberger</name><affiliation><mods:affiliation>Département de Chimie Organique, Université de Genève, 1211 Genève 4</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Helvetica Chimica Acta</title><title level="j" type="alt">HELVETICA CHIMICA ACTA</title><idno type="ISSN">0018-019X</idno><idno type="eISSN">1522-2675</idno><imprint><biblScope unit="vol">59</biblScope><biblScope unit="issue">7</biblScope><biblScope unit="page" from="2335">2335</biblScope><biblScope unit="page" to="2343">2343</biblScope><biblScope unit="page-count">9</biblScope><publisher>WILEY‐VCH Verlag GmbH</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="1976-11-03">1976-11-03</date></imprint><idno type="ISSN">0018-019X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0018-019X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Acetic acid</term><term>Acta</term><term>Alcohol oxidation</term><term>Amer</term><term>Chem</term><term>Chimica</term><term>Chromic acid oxidation</term><term>Column ffap</term><term>Correlation coefficient</term><term>Eliel</term><term>Energy diagram</term><term>Epimeric</term><term>Epimeric alcohols</term><term>Equilibrium constants</term><term>Fasc</term><term>Helvetica</term><term>Helvetica chimica acta</term><term>Isotope effect</term><term>Isotope effects</term><term>Lower limit</term><term>Oxidation rates</term><term>Rate constants</term><term>Regression line</term><term>Sicher</term><term>Sicher correlation</term><term>Sicher plot</term><term>Standard deviation</term><term>Strain difference</term><term>Tlie</term><term>Transition state</term><term>Transition states</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The linear free energy relationship of Sicher for relative reactivity towards chromic acid oxidation (ΔΔG Ox≠) as a function of thermodynamic stability (ΔG eq0) has been reexamined with 23 pairs of epimeric alcohols. The plot of ΔG Ox≠ vs. ΔG eq0 has a slope of 0.8, a correlation coefficient of 0.97 and a standard deviation of 0.23 kcal/mol on ΔΔGOx Ox≠. The limitations of the relationship and the exceptions are discussed.</div></front></TEI><istex><corpusName>wiley</corpusName><keywords><teeft><json:string>chem</json:string><json:string>sicher</json:string><json:string>amer</json:string><json:string>epimeric</json:string><json:string>helvetica</json:string><json:string>tlie</json:string><json:string>fasc</json:string><json:string>acta</json:string><json:string>epimeric alcohols</json:string><json:string>helvetica chimica acta</json:string><json:string>eliel</json:string><json:string>chimica</json:string><json:string>rate constants</json:string><json:string>equilibrium constants</json:string><json:string>transition states</json:string><json:string>oxidation rates</json:string><json:string>transition state</json:string><json:string>strain difference</json:string><json:string>sicher plot</json:string><json:string>acetic acid</json:string><json:string>correlation coefficient</json:string><json:string>isotope effect</json:string><json:string>regression line</json:string><json:string>standard deviation</json:string><json:string>alcohol oxidation</json:string><json:string>isotope effects</json:string><json:string>lower limit</json:string><json:string>energy diagram</json:string><json:string>column ffap</json:string><json:string>chromic acid oxidation</json:string><json:string>sicher correlation</json:string></teeft></keywords><author><json:item><name>Paul Müller</name><affiliations><json:string>Département de Chimie Organique, Université de Genève, 1211 Genève 4</json:string></affiliations></json:item><json:item><name>Jean‐Claude Perlberger</name><affiliations><json:string>Département de Chimie Organique, Université de Genève, 1211 Genève 4</json:string></affiliations></json:item></author><articleId><json:string>HLCA19760590706</json:string></articleId><arkIstex>ark:/67375/WNG-JS08J77N-W</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>The linear free energy relationship of Sicher for relative reactivity towards chromic acid oxidation (ΔΔG Ox≠) as a function of thermodynamic stability (ΔG eq0) has been reexamined with 23 pairs of epimeric alcohols. The plot of ΔG Ox≠ vs. ΔG eq0 has a slope of 0.8, a correlation coefficient of 0.97 and a standard deviation of 0.23 kcal/mol on ΔΔGOx Ox≠. The limitations of the relationship and the exceptions are discussed.</abstract><qualityIndicators><score>5.73</score><pdfWordCount>2938</pdfWordCount><pdfCharCount>17416</pdfCharCount><pdfVersion>1.3</pdfVersion><pdfPageCount>9</pdfPageCount><pdfPageSize>450 x 666 pts</pdfPageSize><refBibsNative>true</refBibsNative><abstractWordCount>66</abstractWordCount><abstractCharCount>426</abstractCharCount><keywordCount>0</keywordCount></qualityIndicators><title>Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title><genre><json:string>article</json:string></genre><host><title>Helvetica Chimica Acta</title><language><json:string>unknown</json:string></language><doi><json:string>10.1002/(ISSN)1522-2675</json:string></doi><issn><json:string>0018-019X</json:string></issn><eissn><json:string>1522-2675</json:string></eissn><publisherId><json:string>HLCA</json:string></publisherId><volume>59</volume><issue>7</issue><pages><first>2335</first><last>2343</last><total>9</total></pages><genre><json:string>journal</json:string></genre><subject><json:item><value>Article</value></json:item></subject></host><namedEntities><unitex><date></date><geogName></geogName><orgName></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName></persName><placeName></placeName><ref_url></ref_url><ref_bibl></ref_bibl><bibl></bibl></unitex></namedEntities><ark><json:string>ark:/67375/WNG-JS08J77N-W</json:string></ark><categories><wos><json:string>1 - science</json:string><json:string>2 - chemistry, multidisciplinary</json:string></wos><scienceMetrix><json:string>1 - natural sciences</json:string><json:string>2 - chemistry</json:string><json:string>3 - general chemistry</json:string></scienceMetrix><scopus><json:string>1 - Physical Sciences</json:string><json:string>2 - Chemistry</json:string><json:string>3 - Inorganic Chemistry</json:string><json:string>1 - Physical Sciences</json:string><json:string>2 - Chemistry</json:string><json:string>3 - Organic Chemistry</json:string><json:string>1 - Physical Sciences</json:string><json:string>2 - Chemistry</json:string><json:string>3 - Physical and Theoretical Chemistry</json:string><json:string>1 - Life Sciences</json:string><json:string>2 - Pharmacology, Toxicology and Pharmaceutics</json:string><json:string>3 - Drug Discovery</json:string><json:string>1 - Life Sciences</json:string><json:string>2 - Biochemistry, Genetics and Molecular Biology</json:string><json:string>3 - Biochemistry</json:string><json:string>1 - Physical Sciences</json:string><json:string>2 - Chemical Engineering</json:string><json:string>3 - Catalysis</json:string></scopus><inist><json:string>1 - sciences appliquees, technologies et medecines</json:string><json:string>2 - sciences biologiques et medicales</json:string><json:string>3 - sciences biologiques fondamentales et appliquees. psychologie</json:string></inist></categories><publicationDate>1976</publicationDate><copyrightDate>1976</copyrightDate><doi><json:string>10.1002/hlca.19760590706</json:string></doi><id>9500174825779537F2FFA54243096576AE8FAF71</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-JS08J77N-W/fulltext.pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-JS08J77N-W/bundle.zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/ark:/67375/WNG-JS08J77N-W/fulltext.tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>WILEY‐VCH Verlag GmbH</publisher><pubPlace>Weinheim</pubPlace><availability><licence>Copyright © 1976 Verlag GmbH & Co. KGaA, Weinheim</licence></availability><date type="published" when="1976-11-03"></date></publicationStmt><notesStmt><note type="content-type" subtype="article" source="article" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</note><note type="publication-type" subtype="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="article"><analytic><title level="a" type="main" xml:lang="en">Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title><author xml:id="author-0000"><persName><forename type="first">Paul</forename><surname>Müller</surname></persName><affiliation><orgName type="department">Département de Chimie Organique</orgName><orgName type="institution">Université de Genève</orgName><address><addrLine>1211 Genève 4</addrLine><country key="CH"></country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Jean‐Claude</forename><surname>Perlberger</surname></persName><affiliation><orgName type="department">Département de Chimie Organique</orgName><orgName type="institution">Université de Genève</orgName><address><addrLine>1211 Genève 4</addrLine><country key="CH"></country></address></affiliation></author><idno type="istex">9500174825779537F2FFA54243096576AE8FAF71</idno><idno type="ark">ark:/67375/WNG-JS08J77N-W</idno><idno type="DOI">10.1002/hlca.19760590706</idno><idno type="unit">HLCA19760590706</idno><idno type="toTypesetVersion">file:HLCA.HLCA19760590706.pdf</idno></analytic><monogr><title level="j" type="main">Helvetica Chimica Acta</title><title level="j" type="alt">HELVETICA CHIMICA ACTA</title><idno type="pISSN">0018-019X</idno><idno type="eISSN">1522-2675</idno><idno type="book-DOI">10.1002/(ISSN)1522-2675</idno><idno type="book-part-DOI">10.1002/hlca.v59:7</idno><idno type="product">HLCA</idno><imprint><biblScope unit="vol">59</biblScope><biblScope unit="issue">7</biblScope><biblScope unit="page" from="2335">2335</biblScope><biblScope unit="page" to="2343">2343</biblScope><biblScope unit="page-count">9</biblScope><publisher>WILEY‐VCH Verlag GmbH</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="1976-11-03"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>The linear free energy relationship of <hi rend="italic">Sicher</hi> for relative reactivity towards chromic acid oxidation (ΔΔ<hi rend="italic">G</hi><math><msubsup><mtext> </mtext><mrow><mtext>Ox</mtext></mrow><mrow><mtext>≠</mtext></mrow></msubsup></math>) as a function of thermodynamic stability (Δ<hi rend="italic">G</hi><math><msubsup><mtext> </mtext><mrow><mtext>eq</mtext></mrow><mrow><mtext>0</mtext></mrow></msubsup></math>) has been reexamined with 23 pairs of epimeric alcohols. The plot of Δ<hi rend="italic">G</hi><math><msubsup><mtext> </mtext><mrow><mtext>Ox</mtext></mrow><mrow><mtext>≠</mtext></mrow></msubsup></math>
<hi rend="italic">vs</hi>. Δ<hi rend="italic">G</hi><math><msubsup><mtext> </mtext><mrow><mtext>eq</mtext></mrow><mrow><mtext>0</mtext></mrow></msubsup></math> has a slope of 0.8, a correlation coefficient of 0.97 and a standard deviation of 0.23 kcal/mol on ΔΔ<hi rend="italic">G</hi><hi rend="subscript">Ox</hi><math><msubsup><mtext> </mtext><mrow><mtext>Ox</mtext></mrow><mrow><mtext>≠</mtext></mrow></msubsup></math>. The limitations of the relationship and the exceptions are discussed.</p></abstract><textClass><keywords rend="articleCategory"><term>Article</term></keywords><keywords rend="tocHeading1"><term>Articles</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-JS08J77N-W/fulltext.txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>WILEY‐VCH Verlag GmbH</publisherName><publisherLoc>Weinheim</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1522-2675</doi><issn type="print">0018-019X</issn><issn type="electronic">1522-2675</issn><idGroup><id type="product" value="HLCA"></id></idGroup><titleGroup><title type="main" xml:lang="de" sort="HELVETICA CHIMICA ACTA">Helvetica Chimica Acta</title><title type="short">HCA</title></titleGroup></publicationMeta><publicationMeta level="part" position="70"><doi origin="wiley" registered="yes">10.1002/hlca.v59:7</doi><numberingGroup><numbering type="journalVolume" number="59">59</numbering><numbering type="journalIssue">7</numbering></numberingGroup><coverDate startDate="1976-11-03">3 November 1976</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="6" status="forIssue"><doi origin="wiley" registered="yes">10.1002/hlca.19760590706</doi><idGroup><id type="unit" value="HLCA19760590706"></id></idGroup><countGroup><count type="pageTotal" number="9"></count></countGroup><titleGroup><title type="articleCategory">Article</title><title type="tocHeading1">Articles</title></titleGroup><copyright ownership="publisher">Copyright © 1976 Verlag GmbH & Co. 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Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Paul</givenNames><familyName>Müller</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Jean‐Claude</givenNames><familyName>Perlberger</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="CH" type="organization"><unparsedAffiliation>Département de Chimie Organique, Université de Genève, 1211 Genève 4</unparsedAffiliation></affiliation></affiliationGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>The linear free energy relationship of <i>Sicher</i> for relative reactivity towards chromic acid oxidation (ΔΔ<i>G</i><math altimg="urn:x-wiley:0018019X:media:HLCA19760590706:tex2gif-stack-1" wiley:location="equation/tex2gif-stack-1.gif"><msubsup><mtext> </mtext><mrow><mtext>Ox</mtext></mrow><mrow><mtext>≠</mtext></mrow></msubsup></math>) as a function of thermodynamic stability (Δ<i>G</i><math altimg="urn:x-wiley:0018019X:media:HLCA19760590706:tex2gif-stack-2" wiley:location="equation/tex2gif-stack-2.gif"><msubsup><mtext> </mtext><mrow><mtext>eq</mtext></mrow><mrow><mtext>0</mtext></mrow></msubsup></math>) has been reexamined with 23 pairs of epimeric alcohols. The plot of Δ<i>G</i><math altimg="urn:x-wiley:0018019X:media:HLCA19760590706:tex2gif-stack-3" wiley:location="equation/tex2gif-stack-3.gif"><msubsup><mtext> </mtext><mrow><mtext>Ox</mtext></mrow><mrow><mtext>≠</mtext></mrow></msubsup></math> <i>vs</i>. Δ<i>G</i><math altimg="urn:x-wiley:0018019X:media:HLCA19760590706:tex2gif-stack-4" wiley:location="equation/tex2gif-stack-4.gif"><msubsup><mtext> </mtext><mrow><mtext>eq</mtext></mrow><mrow><mtext>0</mtext></mrow></msubsup></math> has a slope of 0.8, a correlation coefficient of 0.97 and a standard deviation of 0.23 kcal/mol on ΔΔ<i>G</i><sub>Ox</sub><math altimg="urn:x-wiley:0018019X:media:HLCA19760590706:tex2gif-stack-5" wiley:location="equation/tex2gif-stack-5.gif"><msubsup><mtext> </mtext><mrow><mtext>Ox</mtext></mrow><mrow><mtext>≠</mtext></mrow></msubsup></math>. The limitations of the relationship and the exceptions are discussed.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols</title></titleInfo><name type="personal"><namePart type="given">Paul</namePart><namePart type="family">Müller</namePart><affiliation>Département de Chimie Organique, Université de Genève, 1211 Genève 4</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jean‐Claude</namePart><namePart type="family">Perlberger</namePart><affiliation>Département de Chimie Organique, Université de Genève, 1211 Genève 4</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>WILEY‐VCH Verlag GmbH</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">1976-11-03</dateIssued><copyrightDate encoding="w3cdtf">1976</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">2</extent><extent unit="tables">2</extent><extent unit="references">32</extent></physicalDescription><abstract lang="en">The linear free energy relationship of Sicher for relative reactivity towards chromic acid oxidation (ΔΔG Ox≠) as a function of thermodynamic stability (ΔG eq0) has been reexamined with 23 pairs of epimeric alcohols. The plot of ΔG Ox≠ vs. ΔG eq0 has a slope of 0.8, a correlation coefficient of 0.97 and a standard deviation of 0.23 kcal/mol on ΔΔGOx Ox≠. The limitations of the relationship and the exceptions are discussed.</abstract><relatedItem type="host"><titleInfo><title>Helvetica Chimica Acta</title></titleInfo><titleInfo type="abbreviated"><title>HCA</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Article</topic></subject><identifier type="ISSN">0018-019X</identifier><identifier type="eISSN">1522-2675</identifier><identifier type="DOI">10.1002/(ISSN)1522-2675</identifier><identifier type="PublisherID">HLCA</identifier><part><date>1976</date><detail type="volume"><caption>vol.</caption><number>59</number></detail><detail type="issue"><caption>no.</caption><number>7</number></detail><extent unit="pages"><start>2335</start><end>2343</end><total>9</total></extent></part></relatedItem><identifier type="istex">9500174825779537F2FFA54243096576AE8FAF71</identifier><identifier type="ark">ark:/67375/WNG-JS08J77N-W</identifier><identifier type="DOI">10.1002/hlca.19760590706</identifier><identifier type="ArticleID">HLCA19760590706</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 1976 Verlag GmbH & Co. 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|étape= Corpus
|type= RBID
|clé= ISTEX:9500174825779537F2FFA54243096576AE8FAF71
|texte= Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols
}}
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