Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite

Measurements of kinetic isotope-effects (k*/k) for the oxidation of ten aldoses-1-t with sodium chlorite in acid solution gave values ranging from 0.56 to 0.75, with an average of 0.66. The values show that the C1—H* bond is not ruptured in the rate-determining step. For the reaction, a mechanism is...

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Detalles Bibliográficos
Autores principales: Isbell, Horace S., Sniegoski, Lorna T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: [Gaithersburg, MD] : U.S. Dept. of Commerce, National Institute of Standards and Technology 1964
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5327691/
https://www.ncbi.nlm.nih.gov/pubmed/31834724
http://dx.doi.org/10.6028/jres.068A.027
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author Isbell, Horace S.
Sniegoski, Lorna T.
author_facet Isbell, Horace S.
Sniegoski, Lorna T.
author_sort Isbell, Horace S.
collection PubMed
description Measurements of kinetic isotope-effects (k*/k) for the oxidation of ten aldoses-1-t with sodium chlorite in acid solution gave values ranging from 0.56 to 0.75, with an average of 0.66. The values show that the C1—H* bond is not ruptured in the rate-determining step. For the reaction, a mechanism is proposed which accounts for this fact and for the dependence of the rate of reaction on the concentration of chlorous acid. The mechanism involves formation of a chlorous acid—aldehyde intermediate; this decomposes, giving the aldonic acid and hypochlorous acid. The latter then reacts with more chlorous acid, affording the chlorine dioxide and hydrogen chloride found experimentally.
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spelling pubmed-53276912019-12-10 Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite Isbell, Horace S. Sniegoski, Lorna T. J Res Natl Bur Stand A Phys Chem Article Measurements of kinetic isotope-effects (k*/k) for the oxidation of ten aldoses-1-t with sodium chlorite in acid solution gave values ranging from 0.56 to 0.75, with an average of 0.66. The values show that the C1—H* bond is not ruptured in the rate-determining step. For the reaction, a mechanism is proposed which accounts for this fact and for the dependence of the rate of reaction on the concentration of chlorous acid. The mechanism involves formation of a chlorous acid—aldehyde intermediate; this decomposes, giving the aldonic acid and hypochlorous acid. The latter then reacts with more chlorous acid, affording the chlorine dioxide and hydrogen chloride found experimentally. [Gaithersburg, MD] : U.S. Dept. of Commerce, National Institute of Standards and Technology 1964 1964-06-01 /pmc/articles/PMC5327691/ /pubmed/31834724 http://dx.doi.org/10.6028/jres.068A.027 Text en https://creativecommons.org/publicdomain/zero/1.0/ The Journal of Research of the National Bureau of Standards Section A is a publication of the U.S. Government. The papers are in the public domain and are not subject to copyright in the United States. Articles from J Res may contain photographs or illustrations copyrighted by other commercial organizations or individuals that may not be used without obtaining prior approval from the holder of the copyright.
spellingShingle Article
Isbell, Horace S.
Sniegoski, Lorna T.
Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
title Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
title_full Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
title_fullStr Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
title_full_unstemmed Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
title_short Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
title_sort tritium-labeled compounds. xi. mechanism for the oxidation of aldehydes and aldoses-1-t with sodium chlorite
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5327691/
https://www.ncbi.nlm.nih.gov/pubmed/31834724
http://dx.doi.org/10.6028/jres.068A.027
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