A selectivity study of reaction of the carbonate radical anion with methyl beta- D-cellobioside and methyl beta-D-glucoside in oxygenated aqueous solutions
2006 (English)In: Holzforschung, ISSN 0018-3830, Vol. 60, no 2, 130-136 p.Article in journal (Refereed) Published
In the presence of oxygen, radiolytically generated carbonate radical anions, CO3.-, were reacted with methyl beta-D-cellobioside and methyl beta-D-glucoside. From the ensuing product pattern, it was concluded that CO3 center dot- abstracts hydrogen atoms predominantly from glucosidic C1 - H bonds. This high intramolecular selectivity was rationalised mainly in terms of a polar effect on the transition state of the hydrogen abstraction reaction. The present findings are in sharp contrast to the relative inertness of CO3(center dot-) towards glucosidic C1 - H bonds previously observed in cotton linters. The reasons for this discrepancy are discussed in light of a possible future role of CO3 center dot- as a bleaching agent for pulp.
Place, publisher, year, edition, pages
2006. Vol. 60, no 2, 130-136 p.
carbohydrate, carbonate radical, glucosidic cleavage, hydrogen abstraction, intramolecular, model compounds, selectivity
IdentifiersURN: urn:nbn:se:kth:diva-5268DOI: 10.1515/HF.2006.021ISI: 000236203100003ScopusID: 2-s2.0-33644925334OAI: oai:DiVA.org:kth-5268DiVA: diva2:8207
QC 20101001. Uppdaterad från manuskript till artikel (20101001). Tidigare titel: A Selectivity Study of the Carbonate Radical Anion Reacting with Methyl-β-D-cellobioside and Methyl-β-D-glucoside in Oxygenated Aqueous Solutions