Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols
Identifieur interne : 002256 ( Istex/Curation ); précédent : 002255; suivant : 002257Conformational Analysis and Chromic Acid Oxidation. Oxidation Rates and Equilibrium Constants of Epimeric Alcohols
Auteurs : Paul Müller [Suisse] ; Jean-Claude Perlberger [Suisse]Source :
- 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
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<author><name sortKey="Muller, Paul" sort="Muller, Paul" uniqKey="Muller P" first="Paul" last="Müller">Paul Müller</name>
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<orgName type="university">Université de Genève</orgName>
<country>Suisse</country>
<placeName><settlement type="city">Genève</settlement>
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<author><name sortKey="Perlberger, Jean Laude" sort="Perlberger, Jean Laude" uniqKey="Perlberger J" first="Jean-Claude" last="Perlberger">Jean-Claude Perlberger</name>
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<sourceDesc><biblStruct><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><name sortKey="Muller, Paul" sort="Muller, Paul" uniqKey="Muller P" first="Paul" last="Müller">Paul Müller</name>
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<author><name sortKey="Perlberger, Jean Laude" sort="Perlberger, Jean Laude" uniqKey="Perlberger J" first="Jean-Claude" last="Perlberger">Jean-Claude Perlberger</name>
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<orgName type="university">Université de Genève</orgName>
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<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>
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<publisher>WILEY‐VCH Verlag GmbH</publisher>
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<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>
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<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>
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