Interactions of D-cellobiose with p-toluenesulfonic acid in aqueous solution: A 13C NMR study

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The effects of adding D 2SO 4, and p-toluenesulfonic acid-d to D-cellobiose dissolved in D 2O were investigated at 23 °C by plotting 13C NMR chemical shift changes (Δδ) against the acid to D-cellobiose molar ratio. 13C Chemical shifts of all 18 carbon signals from α and β anomers of D-cellobiose showed gradual decreases due to increasing acidity in aqueous D 2SO 4 medium. The C-1 of the α anomer showed a slightly higher response to increasing D + concentration in the surrounding. In the aqueous p-toluenesulfonic acid-d medium, C-6′ and C-4′ carbons of both α, and β anomeric forms of D-cellobiose are significantly affected by increasing the sulfonic acid concentrations, and this may be due to a 1:1 interaction of p-toluenesulfonic acid-d with the C-6′, C-4′ region of the cellobiose molecule. © 2011 Elsevier Ltd. All rights reserved.

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