Citation: Li Qianggen, Xiang Shikai, Mao Shuang, Ren Yi. Theoretical Investigations on the Intramolecular N-Arylation Mechanism and Reactivity for the Synthesis of Benzimidazoles by Base-Catalyzed[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 608-616. doi: 10.6023/cjoc201609020 shu

Theoretical Investigations on the Intramolecular N-Arylation Mechanism and Reactivity for the Synthesis of Benzimidazoles by Base-Catalyzed

Li Qianggen ^a,*,, ,
Xiang Shikai ^a ,
Mao Shuang ^a ,
Ren Yi ^b,*,,

a.
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068
b.
College of Chemistry, Sichuan University, Chengdu 610064

Corresponding author: Li Qianggen, liqgen@sina.com Ren Yi, renyi@scu.edu.cn
Received Date: 18 September 2016
Revised Date: 7 December 2016

Fund Project: the Research Funds of Sichuan Normal University 16ZP10Project supported by the National Natural Science Foundation of China 21202109the Research Fund of Department of Education, of Sichuan Province 13ZB0160

Figures(7)

Quantum chemical studies on the intramolecular N-arylation mechanism and reactivity of N-(2-halogen phenyl)-N'-phenyl ethyl amidines in dimethyl sulfoxide (DMSO) for the synthesis of benzimidazoles by base-catalyzed have been performed at MP2/6-311+G^**//B3LYP/6-311+G^** level of theory. The results indicate that the mechanism of the title reactions is not the radical mechanism or stepwise S_NAr pathway, but the concerted S_NAr pathway with a transition state, which is compared with the conclusion of Bolm et al. The reactivity of the title reactions can not be interpreted by the geometric looseness or natural population analysis. Multi parameter fitting reveals that the reactivity of the title reactions is controlled mostly by the regional nucleophilicity index ω_N10^- of the nucleophile N10 atom or highest occupied molecular orbital energy E_HOMO of the reactant, the other factor is the charges of the nucleophilic atom N10, while the charges of the C2 atom and the geometric looseness L% have almost no effect on the reaction energy barrier. The relative energies and the reactivity of the title reactions attained at MP2/6-311+G^**//B3LYP/6-311+G^** level of theory are better agreement with the experimental results compared with the other methods.
- intramolecular N-arylation,
- N-(2-halogen phenyl)-N'-phenyl ethyl amidines,
- reaction mechanism,
- S_NAr reaction,
- B3LYP,
- nucleophilicity index
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