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 MoreBeijing Zhongshuo Pharmaceutical T & D Co.,Ltd
Contact:0086-10-64430626
Address:ea No 16, HEPINGLI,DONGCHENG DISTRICT,BEIJING,P.R.CHINA.
Shanghai Forever Synthesis Co.,Ltd.
Contact:021-61124658
Address:Zhoukang Road,Pudong New District,Shanghai,China
Huaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
website:http://www.amadischem.com
Contact:86-571-89925085
Address:Watts Cosine.No.166.Xiangmao Road.
Shanghai Hohance Chemical Co., ltd
Contact:13914753421
Address:Fl.5；Bld. 70, Lane 1500; Xinfei Road
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)
