Interactions of D-cellobiose with p-toluenesulfonic acid in aqueous solution: a (13)C NMR study.
The effects of adding D(2)SO(4), and p-toluenesulfonic acid-d to D-cellobiose dissolved in D(2)O were investigated at 23°C by plotting (13)C NMR chemical shift changes (Δδ) against the acid to D-cellobiose molar ratio. (13)C 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(2)SO(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.
Department of Chemistry, Prairie View A&M University, Prairie View, TX 77446, USA. asamarasekara@pvamu.edu
Ananda S
AS
Amarasekara
Onome S
OS
Owereh
Brian
B
Ezeh
D001557:Benzenesulfonates / Q000737:chemistry*; D002475:Cellobiose / Q000737:chemistry*; D017666:Deuterium Oxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents / Q000737:chemistry; D013464:Sulfuric Acids / Q000737:chemistry
D001557:Benzenesulfonates; D012997:Solvents; D013464:Sulfuric Acids; D002475:Cellobiose; D017666:Deuterium Oxide; C033158:sulfuric acid; C029501:4-toluenesulfonic acid