18O and secondary2H kinetic isotope effects confirm the existence of two pathways for acid-catalysed hydrolyses of α-arabinofuranosides

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Abstract
The 18O kinetic isotope effect on the HClO4-catalysed hydrolysis of 4-nitrophenyl [1-18O]-α-arabinofuranoside (k16/k18) is 1.023 ± 0.003 at 80.0 °C; that for isopropyl (1-18O]-α-arabinofuranoside is 0.988 at 30.2 °C and the secondary deuterium effect on the hydrolysis of [2-2H]propan-2-yl α-arabinofuranoside (kH/kD) is 0.979. The nitrophenyl glycoside reacts with exocyclic C–O cleavage and the propan-2-yl glycoside by endocyclic C–O cleavage.