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Theoretical Study on Reaction Mechanism of Tautomerization of Indazole and 3-halogeno-indazole
Hai-yan Yu,Bao-zong Li*,Yong-min Guo
Author NameAffiliationE-mail
Hai-yan Yu Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006, China; Department of Chemistry, Yancheng Normal College, Yancheng 224002, China  
Bao-zong Li* Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006, China  
Yong-min Guo Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006, China ymguo@suda.edu.cn 
Abstract:
The molecular structures of indazole and 3-halogeno-indazole tautomers were calculated by the B3LYP method at the 6-311G** level, both in the gaseous and aqueous phases, with full geometry optimization.The geometry and electronic structure of the tautomers of indazole, 3-halogeno-indazole and their transition states were obtained. The Onsager solvate theory model was employed for the aqueous solution calculations.The results of the calculation indicated that the N1-H form of the studied molecule is more stable than that of the N2-H form. The influences of the different 3-halogeno and solvent effects on the geometry, energy,charge and activation energy were discussed. The reaction mechanism of the tautomerization of indazole and 3-halogeno-indazole was also studied and a three-membered cyclic transition state of the tautomer reaction has been obtained.
Key words:  3-halogeno-indazole, Tautomers, Transition states, Activation energy, DFT
FundProject:
吲唑、3-卤代吲唑互变异构反应机理的理论研究
于海艳,李宝宗*,国永敏
摘要:
在密度泛函B3LYP/6-311G**水平上对气相和水相中吲唑、3-卤代(-F、-Cl和-Br)吲唑互变异构体进行几何构型全自由度优化, On-sager反应场溶剂模型用于水相计算.计算结果显示,在气相和水相中吲唑、3-卤代吲唑的N1-H形式比其相应的N2-H形式稳定.进一步研究了吲唑、3-卤代吲唑互变异构的反应机理,求得了N(1)、N(2)、H(10)组成三元环且迁移原子H(10)偏离分子平面60°?70°的过渡态结构.探讨了不同的3-取代基团和溶剂化效应对互变异构体的几何结构、能量、电荷分布以及互变异
关键词:  3-卤代吲唑, 互变异构体, 过渡态, 活化能, 密度泛函理论
DOI:10.1360/cjcp2006.19(3).233.5
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