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Issue 8, 1985
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18O and secondary 2H kinetic isotope effects confirm the existence of two pathways for acid-catalysed hydrolyses of α-arabinofuranosides

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.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1985, 1233-1236
Article type
Paper

18 O and secondary 2H kinetic isotope effects confirm the existence of two pathways for acid-catalysed hydrolyses of α-arabinofuranosides

A. J. Bennet, M. L. Sinnott and W. S. S. Wijesundera, J. Chem. Soc., Perkin Trans. 2, 1985, 1233
DOI: 10.1039/P29850001233

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