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 MoreSINO Industries Company Limited(expird)
Contact:86-29-85369724
Address:No.111, Jiefang Road, Xi’an, China
Suzhou Howsine Biological Technology Co.,Ltd(expird)
website:http://www.howsine.com
Contact:86-512-67262751
Address:No 3,Weihua Road ,Suzhou Industrial Park ,Jiangsu ,China.
SHIFANG SUHONG CHEMICAL CO.,LTD
Contact:+86-838-2224563
Address:Room 1207 Zongchen Sunshine No.128 Taishan South Road,Deyang City,Sichuan China
Sanming Coffer Fine Chemical Industrial Co., Ltd
website:http://www.cofferxm.com/
Contact:+86-598-5853979
Address:Jin-sha Yuan Chuang-ye Park,Hi-Tech Development Zone,Sanming City P.R.China
Tianjin SPHINX SCIENTIFIC LAB.
Contact:+86-022-66211289
Address:Tianda high-tech Park. No.80,the 4th Avenue
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)
