Abstract
In acidic aqueous solutions, the protonation of gluconate is coupled with the lactonization of gluconic acid. With a decrease of pC H, two lactones (δ- and γ-) are sequentially formed. The δ-lactone forms more readily than the γ-lactone. In 0.1 mol⋅L−1 gluconate solutions, if pC H>2.5 then only the δ-lactone is generated. When the pC H is decreased below 2.0, formation of the γ-lactone is observed although the δ-lactone still predominates. In solutions with I=0.1 mol⋅L−1 NaClO4 and room temperature, the deprotonation constant of the carboxylic group was determined to be log 10 K a=3.30±0.02 using the NMR technique, and the δ-lactonization constant obtained by batch potentiometric titrations was log 10 K L=−(0.54±0.04). Using ESI-MS, the rate constants for the δ-lactonization and the reverse hydrolysis reaction at pC H≈5.0 were estimated to be k 1=3.2×10−5 s−1 and k −1=1.1×10−4 s−1, respectively.
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Zhang, Z., Gibson, P., Clark, S.B. et al. Lactonization and Protonation of Gluconic Acid: A Thermodynamic and Kinetic Study by Potentiometry, NMR and ESI-MS. J Solution Chem 36, 1187–1200 (2007). https://doi.org/10.1007/s10953-007-9182-x
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DOI: https://doi.org/10.1007/s10953-007-9182-x