Kinetic and Theoretical Study on the Ion/Molecule Reactions of Methoxymethyl Cation with Ammonia

Article abstract of DOI:10.1021/ja00236a001

The reaction between C2H5O⁺ and NH3 is investigated by using the ion-trapping technique.Rate constants of reactions 3, 4, and 5 are determined.Their potential energy profiles are sought by use of the ab initio MO calculation.Reaction 3 gives the products methanol and protonated methylenimine.It is composed of the nucleophilic addition of NH3 to the carbonyl carbon and the subsequent 1,3-proton shift.Reaction 4 gives formaldehyde and protonated methylamine.It is of the S_N2 type.Reaction 5 gives ammonium ion and ethylene oxide.The last reaction is of the specific pattern in the gas phase, although the reverse reaction involves the popular mechanism of the electrophilic ring cleavage.