Abstract
The acid-catalyzed hydrolysis of sucrose to glucose and fructose was investigated by DFT calculations. Protonations to three ether oxygen atoms of the sucrose molecule, A, B, and (C, D), were compared. Three (B, the fructosyl-ring oxygen protonation; C, protonation to the bridge oxygen of the glycosidic bond for the glucosyl-oxygen cleavage; and D, protonation to that for the fructosyl-oxygen cleavage) gave the fragmentation. Paths B, C, and D were examined by the use of the sucrose molecule and H3O(+)(H2O)13. The path B needs a large activation energy, indicating that it is unlikely. The fragmentation transition state (TS1) of path C needs almost the same activation energy as that of path D. The isomerization TS of Int(C) → Int(D), TS(C → D), was also obtained as a bypass route. The present calculations showed that the path via the fructosyl-oxygen cleavage (D) is slightly (not absolutely) more favorable than that via the glucosyl-oxygen cleavage (C).
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