Theoretical study on the addition reaction between propadienylidene and methyleneimine

Authors : Mengyuan WANG, Yungang CHEN, Shanshan DING, Yingde WANG

Pages : 335-343

Doi:10.3906/kim-1203-55

View : 12 | Download : 4

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The reaction mechanism between propadienylidene and methyleneimine was systematically investigated employing the second-order Møller--Plesset perturbation theory insert ignore into journalissuearticles values(MP2); method with the 6 -- 31 + G* basis set. Geometry optimization, vibrational analysis, and energy property of the involved stationary points on the potential energy surface were calculated. The energies of the different species were corrected by single point energy calculations at the CCSD insert ignore into journalissuearticles values(T); // MP2 / 6 -- 31 + G* level. From the surface energy profile, one important initial intermediate characterized by a 3-membered ring structure was located via a transition state firstly. After that, 3 different products possessing 3- and 4-membered ring characters were obtained through corresponding reaction pathways. In the first reaction pathway insert ignore into journalissuearticles values(1);, a 3-membered ring alkyne compound was obtained. A 4-membered ring conjugated diene compound was produced in the other 2 reaction pathways, pathways insert ignore into journalissuearticles values(2R); and insert ignore into journalissuearticles values(2L);. The energy barrier of the rate-determining step of pathway insert ignore into journalissuearticles values(1); is higher than those of the pathways insert ignore into journalissuearticles values(2R); and insert ignore into journalissuearticles values(2L);, where the ultimate products of pathways insert ignore into journalissuearticles values(2R); and insert ignore into journalissuearticles values(2L); are more stable than that of pathway insert ignore into journalissuearticles values(1);. Therefore, the dominating product of the addition reaction between propadienylidene and methyleneimine should be the 4-membered ring conjugated diene compound.
Keywords : Propadienylidene, methyleneimine, reaction mechanism, MP2 method