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

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

Research output: Contribution to journalArticleScientificpeer-review

9 Citations (Scopus)

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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Lactones
Acidity
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
Acids
Deprotonation
Hydroxyl Radical

Keywords

  • Xylonic acid
  • lactonization
  • protonation

Cite this

Hummel, M. ; Leppikallio, M. ; Heikkinen, S. ; Niemelä, Klaus ; Sixta, H. / Acidity and lactonization of xylonic acid : A nuclear magnetic resonance study. In: Journal of Carbohydrate Chemistry. 2011 ; Vol. 29, No. 8-9. pp. 416-428.
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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).",
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Acidity and lactonization of xylonic acid : A nuclear magnetic resonance study. / Hummel, M.; Leppikallio, M.; Heikkinen, S.; Niemelä, Klaus; Sixta, H.

In: Journal of Carbohydrate Chemistry, Vol. 29, No. 8-9, 2011, p. 416-428.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Acidity and lactonization of xylonic acid

T2 - A nuclear magnetic resonance study

AU - Hummel, M.

AU - Leppikallio, M.

AU - Heikkinen, S.

AU - Niemelä, Klaus

AU - Sixta, H.

PY - 2011

Y1 - 2011

N2 - 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).

AB - 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).

KW - Xylonic acid

KW - lactonization

KW - protonation

U2 - 10.1080/07328303.2011.567424

DO - 10.1080/07328303.2011.567424

M3 - Article

VL - 29

SP - 416

EP - 428

JO - Journal of Carbohydrate Chemistry

JF - Journal of Carbohydrate Chemistry

SN - 0732-8303

IS - 8-9

ER -