Journal of Organic Chemistry p. 4921 - 4924 (1985)
Update date:2022-08-16
Topics:
Bunton, Clifford A.
Mhala, Marutirao M.
Moffatt, John R.
Spontaneous hydrolyses of benzenesulfonyl chlorides are inhibited by micelles of cetyltrimethylammonium chloride (CTACl), sodium dodecyl sulfate (SDS), and N-hexadecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate (SB3-16).The rate constants for hydrolyses of fully bound substrates are similar in CTACl and SB3-16.The rate constants in CTACl (k+) and SDS (k-) depend on the electronic effects of the 4-substituents and k+/k- increases in the sequence MeO < Me < H < Br < NO2.These micellar charge effects are ascribed to changes in the extents of bond-making and -breaking in the transition state.Hydrolysis in micellized N-dodecyl-N,N-dimethylglycine (B1-12) is inhibited, but this effect is offset by nucleophilic participation by the carboxylate moiety.Electron-withdrawing substituents strongly favor nucleophilic participation and for the 4-bromo and 4-nitro derivatives second-order rate constants in zwittwerionic betaine micelles of B1-12 are similar to those for reaction with nonmicellized N,N,N-trimethylglycine in water.
View MoreYixing Bluwat Chemicals Co., Ltd.
Contact:+86 510 87821568
Address:Yongan Road, Yixing Chemical Industrial Park, Yixing, Jiangsu, China
Contact:18698110882
Address:1303 No2 building,LuoMa Garden,YongAn Road,Hexi District,Tianjin city
Jurong Huaheng Natural Biological Products Factory
website:http://www.risebiochem.com
Contact:+86-13921007726
Address:Chuncheng town,Jurong city,Jiangsu province,China
Jiangsu Fengshan Group Co., Ltd.
Contact:86-25-86558671
Address:1903,Central International Mansion 105-6 North Zhongshan Road, Nanjing, China
Hubei Lansun Biochemical Pharmaceutical Co., Ltd
Contact:714-6395977
Address:No. 81 Pengcheng Avenue, economic and technological development zone, Huangshi City, Hubei Province,China
Doi:10.1016/j.bmc.2019.115299
(2020)Doi:10.1021/bi00578a042
(1979)Doi:10.1002/cctc.202000508
(2020)Doi:10.1039/d0gc04199h
(2021)Doi:10.1021/acs.inorgchem.5b00856
(2015)Doi:10.1016/S0957-4166(00)86218-7
(1994)