International Journal of Chemical Studies
Vol. 5, Issue 1 (2017)
Mechanisms of acid catalyzed E/Z isomerization of methyl O-methylbenzohydroximate
Author(s): Houquan Dai, Diana C Canseco and James E Johnson
Abstract: An investigation into the acid-catalyzed E/Z isomerization of methyl O-methylbenzohydroximate in acetonitrile has been carried out. The data allows one to calculate the pKb of methyl O-methylbenzohydroximate. The barrier to rotation of the iminium ion obtained at high concentrations of triflic acid is 22 kcal/mole at 25 °C. The isomerization in hydrochloric acid was determined to take place by nucleophilic catalysis. The pKa of dibromoacetic acid was determined to be 13.58. A similar study was carried out on methyl O-methylbenzothiohydroximate. The barrier to rotation of the immium ion is 25 kcal/mol and the pKb of the thiohydroximate is 23.7.
Pages: 46-49 | 982 Views 46 Downloads
How to cite this article:
Houquan Dai, Diana C Canseco, James E Johnson. Mechanisms of acid catalyzed E/Z isomerization of methyl O-methylbenzohydroximate. Int J Chem Stud 2017;5(1):46-49.