Acta Chimica Sinica ›› 2006, Vol. 64 ›› Issue (4): 278-282. Previous Articles     Next Articles

Original Articles

可乐定分子构象异构和互变异构的理论研究

李宝宗*   

  1. (苏州大学化学化工学院 苏州 215123)
  • 收稿日期:2005-05-26 修回日期:2005-10-24 出版日期:2006-02-28 发布日期:2006-02-28
  • 通讯作者: 李宝宗

Theoretical Investigation on Conformational Isomerization and Tautomerization of Clonidine

LI Bao-Zong*   

  1. (School of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123)
  • Received:2005-05-26 Revised:2005-10-24 Online:2006-02-28 Published:2006-02-28
  • Contact: LI Bao-Zong

The conformational analysis of the various tautomers of clonidine in both neutral and protonated forms have been investigated using HF/6-31G* method. The conformers located at minima by HF/6-31G* calculation were re-optimized by B3LYP/6-31G** method without any constraints. The B3LYP/6-31G** calculations on the tautomerism of clonidine in an aqueous medium using Onsager solvation theory model have shown that the solvent does not change the relative stability of the individual tautomers of this drug and the neutral molecule of clonidine exists as the more stable imino tautomer in the gas and aqueous phases. The results are in good agreement with available experimental ones. The protonation and solvent effects were examined by analyzing the change of molecular geometric and energy parameters. The mechanism of clonidine conformational isomerization and tautomeric reaction has been studied and the geometric parameters of transition states have been located by B3LYP/6-31G**. In order to evaluate conjugation effects of chlorobenzene on distribution of the clonidine tautomers, we have studied the mechanism of 2-aminoimidazoline tautomeric reaction by B3LYP/6-31G** method.

Key words: clonidine, tautomerization, conformational isomerization, density functional theory method, self-consistent reaction field method