TY - JOUR
T1 - The hydrolytic reactivity of β-sultams
AU - Baxter, Nicholas J.
AU - Laws, Andrew P.
AU - Rigoreau, Laurent
AU - Page, Michael I.
PY - 1996
Y1 - 1996
N2 - N-Methyl β-sultam undergoes acid- and base-catalysed hydrolysis in water at 30 °C and I = 1.0 mol dm-3 with kH+ = 2.79dm3 mol-1s-1 and KOH = 1.38 × 10-2 dm3 mol-1 s-1. These second-order rate constants are approximately 109 and 107, respectively, greater than those for a similar acyclic sulfonamide. The entropy of activation for the acid-catalysed hydrolysis of the β-sultam is -80 J K-1 mol-1 which may be indicative of unimolecular ring opening, whereas that for the base-catalysed reaction, - 184 J K-1 mol-1, is consistent with a bimolecular process.
AB - N-Methyl β-sultam undergoes acid- and base-catalysed hydrolysis in water at 30 °C and I = 1.0 mol dm-3 with kH+ = 2.79dm3 mol-1s-1 and KOH = 1.38 × 10-2 dm3 mol-1 s-1. These second-order rate constants are approximately 109 and 107, respectively, greater than those for a similar acyclic sulfonamide. The entropy of activation for the acid-catalysed hydrolysis of the β-sultam is -80 J K-1 mol-1 which may be indicative of unimolecular ring opening, whereas that for the base-catalysed reaction, - 184 J K-1 mol-1, is consistent with a bimolecular process.
UR - http://www.scopus.com/inward/record.url?scp=0001042716&partnerID=8YFLogxK
U2 - 10.1039/P29960002245
DO - 10.1039/P29960002245
M3 - Article
AN - SCOPUS:0001042716
SP - 2245
EP - 2246
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 0300-922X
IS - 11
M1 - 6/05903A
ER -