Journal of the Chemical Society. Perkin transactions II p. 2111 - 2116 (1990)
Update date:2022-08-04
Topics:
Bowden, Keith
Bromley, Keith
The rate coefficients for the alkaline hydrolysis of a series of N-methyl, N-phenyl and bicyclo lactams, penicillins and N-alkyl-N-methylacetamides in water or in aqueous dimethyl sulphoxide have been measured at several temperatures.The reactions were first order in both substrates and base.The reactivities are related to the structures of the substrates, especially N-substitution, ring size and fused ring effects.The reactivities, as well as the activation parameters, kinetic solvent and solvent isotope effects, are used to suggest the detailed mechanisms.All the β-lactams appear to react with rate-determining addition of hydroxide anion; while the N-alkyl γ- and δ-lactams and N-alkyl-N-methylacetamides have rate-determining ring fission of the tetrahedral adduct, assisted by water-catalysis.The reactivity of penicillin in alkaline hydrolysis has been analysed by studies of model compounds.These show that the increased reactivity of the penicillin β-lactam ring arises from the direct action of the fused ring structure and the acetylamino side chain.
View MoreCerametek Materials（ShenZhen）Co., Ltd.
Contact:+86-755-2324.2554
Address:A3-#9, YongChuan Street, Suite 501
FREEBARQUE DEVELOPMENT GROUP LIMITED
Contact:+86(0)10-5109 5335 or 5109 5345
Address:Room602,Block1-B,LINGDI OFFICE,NO.13 BEIYUAN ROAD
Shandong Ailitong New Material Co.,Ltd
Contact:+86-536-3226266
Address:zhongjia village, putong town , qingzhou city,Shandong Province,China
Contact:0792-8228321
Address:10TH Floor No.121 binjiang Road Xunyang District
Chengdu Pukang Biotechnology Co., Ltd
Contact:+86-28-82550498
Address:No. 558 Rulin Road,Xinjin county,Chengdu city, China
Doi:10.1021/jf0114684
(2002)Doi:10.1016/S0040-4039(00)98221-2
(1985)Doi:10.1002/anie.200801030
(2008)Doi:10.1021/jo01281a015
(1967)Doi:10.1021/ja803086r
(2008)Doi:10.1016/j.carres.2008.01.013
(2008)
