| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5277875 | Tetrahedron Letters | 2010 | 4 Pages |
Abstract
The kinetics of hydrolysis of the medicinally important sulfamate ester EMATE have been probed over a wide pH range and into moderately strong base (H_ region). Analysis of the pH/H_-rate profile, measurements of pKas, solvent-reactivity, kinetic isotope effects and determination of activation data reveal that in the pH range from â¼1 to â¼8 an SN2 (S) solvolytic mechanism is followed and after the pKa of EMATE (pKa â¼9) is passed, a second pathway showing a first-order dependence on base operates and an E1cB mechanism is supported.
Graphical abstractTwo hydrolysis pathways for the biologically-important sulfamate ester EMATE have been established.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
William J. Spillane, Jean-Baptiste Malaubier,