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

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

doi:10.1080/07328303.2011.567424

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 (K_L = 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 language	English
Pages (from-to)	416-428
Number of pages	13
Journal	Journal of Carbohydrate Chemistry
Volume	29
Issue number	8-9
DOIs	https://doi.org/10.1080/07328303.2011.567424
Publication status	Published - 2011
MoE publication type	A1 Journal article-refereed

Keywords

Xylonic acid
lactonization
protonation

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10.1080/07328303.2011.567424

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@article{ff674e5eccb64a3484c0a93881a8c6de,

title = "Acidity and lactonization of xylonic acid: A nuclear magnetic resonance study",

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).",

keywords = "Xylonic acid, lactonization, protonation",

author = "M. Hummel and M. Leppikallio and S. Heikkinen and Klaus Niemel{\"a} and H. Sixta",

year = "2011",

doi = "10.1080/07328303.2011.567424",

language = "English",

volume = "29",

pages = "416--428",

journal = "Journal of Carbohydrate Chemistry",

issn = "0732-8303",

publisher = "Taylor \& Francis",

number = "8-9",

}

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

SN - 0732-8303

VL - 29

SP - 416

EP - 428

JO - Journal of Carbohydrate Chemistry

JF - Journal of Carbohydrate Chemistry

IS - 8-9

ER -

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

Abstract

Keywords

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