KINETICS AND MECHANISM OF REACTION OF cis-α,β-DINITROSTILBENE WITH MORPHOLINE

Article abstract of DOI:10.1007/BF00863913

Reaction of cis-α,β-dinitrostilbene (substrate) with morpholine (reagent) in n-hexane leads to cis-α-nitro-β-morpholinostilbene (end product).The process is of first order with respect to the substrate and second order with respect to the reagent.Possible reaction mechanisms are analyzed, and it is established that the following are most probable on the basis of kinetic patterns and stereochemistry: development of a charge transfer complex having a hydrogen bond between the substrate nitro group and reagent amino group; reaction of the complex with a second reagent molecule and formation of a carbanion (this stage determines the overall reaction rate); and detachment of a nitrite ion from the nitrocarbanion and its protonation to form the end product. Keywords: cis-α,β-dinitrostilbene, α-nitro-β-morpholinostilbene, nucleophilic vinylic substitution, hydrogen bond, carbanion, reaction route.