Abstract
A kinetic investigation of the interchange process in the equilibrium between the Z- and E-isomers of a stable phosphorus ylide involving 2-mercaptobenzimidazole has been undertaken by the 1H NMR technique. Kinetic and activation parameters such as k–1, k1, ktotal, Ea1, Ea–1, Eatotal, ΔS#, ΔH# and ΔG# along with the thermodynamic parameters Ke, ΔH°, ΔG° and ΔS° were obtained from the experimental data for the forward and reverse reactions.
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