Stereoelectronic Effects at Oxygen. A Very Large Effect on the Hydrolysis of a Conformationally Locked Acetal: Implications for β-Glycosidase Mechanism

DOI: 10.1039/P29830001637

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1637 - 1640 (1983)

Update date:2022-08-03

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Authors:

Briggs, Andrew J.

Evans, Christopher M.

Glenn, Robert

Kirby, Anthony J.

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Article abstract of DOI:10.1039/P29830001637

Acetal <6; R=2,4-(NO2)2C6H3> is rigidly fixed in the equatorial conformation.As a result the lone-pair electrons on the ring oxygen cannot assist C-OR cleavage, and the compound is hydrolysed ca. 10¹³ times more slowly than a comparable axial t

Full text of DOI:10.1039/P29830001637

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