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
Descripción
Sumario: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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