Journal of the Chemical Society. Perkin transactions II p. 1318 - 1325 (1980)
Update date:2022-08-04
Topics:
Chandler, Anne
Hegarty, Anthony F.
McCormack, Margaret T.
The hydrolysis of 1-(N-t-butylformimidoyl)imidazole (7a) to t-butylformamide and imidazole has been examined in the absence of buffer species at 25 deg C in water.The rate of hydrolysis was pH-independent at pH 7-14 and reaction in this region is shown to occur via HO- attack on the protonated substrate (whose pKa is 5.0; protonation site, imidazole nitrogen).Alternative mechanisms such as H2O attack on the neutral substrate and reaction via the zwitterion (15) were eliminated using solvent isotope effect, deuterium labelling, and substituent effects.Below pH 6 acid catalysis of hydrolysis is observed due to H2O reaction with the protonated substrate (pH 4-6) and with the diprotonated substrate (pH 0-4); at pH 0, t1/2 for hydrolysis is <10-2s.The N-arylformamidines (7b) and (7c) react via similar acid catalysed pathways but a new reaction (identified as HO- attack on the amidine) occurs in base, in preference to the pH independent pathways. p-Nitrophenylformamide
Nantong Baokai Chemical Co., Ltd (Hangzhou Baokai Bio-Chemicals Co.,Ltd.)
Contact:+86-513-83886111
Address:No. 68 Suzhou road ,Binjiang Fine Chemical Industrial Park , Beixin town, Qidong city ,Jiangsu province
Guangzhou Chemical Reagent Factory
Contact:+86-20-8435 9820 or 8435 7345
Address:Southern Guangzhou, Guangdong, China
website:https://www.sinoshiny.com/products
Contact:+86-20-62802632;62802633
Address:Room 330 GIGCAS Building,No.511 Kehua Street,Tianhe District
Chemsky（shanghai）International Co.,Ltd.
Contact:0
Address:0
HANGZHOU GOPHER CHEM-TECH CO.,LTD
Contact:86-189-58111780
Address:Da Cheng Ming Zuo Plaza,Xiaoshan District
Doi:10.1002/(SICI)1521-3773(19981231)37:24<3392::AID-ANIE3392>3.0.CO;2-G
(1999)Doi:10.1002/hlca.19510340122
(1951)Doi:10.1248/cpb.32.4893
(1984)Doi:10.1021/jo00317a026
(1981)Doi:10.1016/0022-1902(64)80290-6
(1964)Doi:10.1016/S0040-4039(00)77396-5
(1980)
