Journal of the Chemical Society. Perkin transactions II p. 163 - 168 (1986)
Update date:2022-08-03
Topics:
Chrystiuk, Edwin
Jusoh, Adelina
Santafianos, Dino
Williams, Andrew
Equilibrium constants for the reaction of phenoxide ions with 2-phenyloxazol-5(4H)-one at 25 deg C and 1M ionic strength obey a Broensted relationship (log kOH/kArO = log K' = -173pKArOH - 15.81) and are not subject to steric effects from ortho-substituents.Both forward and reverse rate parameters exhibit steric effects, and the Broensted equations for meta- and para-substituted species are log kOH = -0.81 pKArOH + 9.75, and log kArO = 0.95pKArOH - 6.40.There is no break in the Broensted line in the region of pKArOH 5-11, consistent with a single transition-state.An upward deviation exists for oxyanions with low basicity (pKXOH < 5); one of these oxyanions, betaine, has a solvent deuterium oxide isotope effect for its reaction with the oxazolone greater than 2, consistent with a general base mechanism for attack for these species.The results for nucleophilic attack of phenolate anions are in agreement with a concerted displacement at the carbonyl group.
View MoreContact:+86-021-58123769
Address:No.780 of Cailun Road,Zhangjiang Hi-tech Park,Pudong,Shanghai
Contact:+86-519-86339586，13584329896
Address:Changzhou Scientific and Education Park
Hunan Haili Chemical Industry Co.,Ltd.
Contact:+86-731-85521860
Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China
Daicel Chiral Technologies (China)CO.,LTD
Contact:021-5046-0086*8
Address:Part C, FL 5, the 16th Building, No. 69, XiYa Road, WaiGaoQiao Free Trade Zone, Shanghai, 200131, P.R.China
Guangzhou Puho Pharmaceutical Technology Co. Ltd.
Contact:86-20-29848035/29848075
Address:No.166, Chaoyang East Road, Panyu District, Guangzhou City, Guangdong Province
Doi:10.1039/c5cc10472f
(2016)Doi:10.1039/c7tc00733g
(2017)Doi:10.1039/DT9900003051
(1990)Doi:10.1021/om200508k
(2011)Doi:10.2174/157018011797655269
(2011)Doi:10.1007/BF00961500
(1990)
