Acidity and lactonization of xylonic acid: A nuclear magnetic resonance study

M. Hummel, M. Leppikallio, S. Heikkinen, Klaus Niemelä, H. Sixta

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Abstract

In acidic aqueous solutions the xylonic acid/xylonate equilibrium is coupled with the formation of the γ- and δ-lactones. The γ-lactone is formed more readily, whereas the δ-lactone can only be observed in traces at very low pH values (<2.5). By means of 13C NMR, both the lactone hydrolization constant and the acid dissociation constant could be determined (KL = 4.08,   = 3.65 ± 0.34). Further, a second deprotonation of one of the hydroxyl groups could be observed at very high pH (  = 13.3 ± 0.76).
Original languageEnglish
Pages (from-to)416-428
Number of pages13
JournalJournal of Carbohydrate Chemistry
Volume29
Issue number8-9
DOIs
Publication statusPublished - 2011
MoE publication typeA1 Journal article-refereed

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Keywords

  • Xylonic acid
  • lactonization
  • protonation

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