title: New insight into the formation mechanism of imidazolium-based halide salts.
abstract: By performing density functional theory calculations, the Menshutkin reaction between the N-methyl imidazole with chloroethane is reexamined to rationalize the experimental discovery. The calculated results show that the reaction proceeds via a S(N)2 mechanism with a barrier of 119.1 kJ mol(-1) which is much lower than that reported in previous literature according to a five-membered transition state mechanism. Moreover, it is found that the barrier is further reduced to 98.1 kJ mol(-1) in toluene solution. The present result validates the experimental finding that the Menshutkin reaction for synthesizing N-alkyl imidazolium halide salts proceed smoothly at lower heating temperature.
authors.affiliation: Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Xueying
authors.initials: X
authors.lastname: Zhu
authors.forename: Dongju
authors.initials: D
authors.lastname: Zhang
authors.forename: Chengbu
authors.initials: C
authors.lastname: Liu
mesh_terms: D007093:Imidazoles / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D007093:Imidazoles; D052578:Ionic Liquids; D012997:Solvents