高等学校化学学报 ›› 1999, Vol. 20 ›› Issue (11): 1784.

• 研究简报 • 上一篇    下一篇

3-X-2(1H)-吡啶酮互变异构体系的理论计算

邹建卫, 李江波, 朱龙观, 俞庆森, 林瑞森   

  1. 浙江大学化学系, 杭州 310027
  • 收稿日期:1998-10-22 出版日期:1999-11-24 发布日期:1999-11-24
  • 通讯作者: 邹建卫,男,27岁,博士研究生.
  • 作者简介:邹建卫,男,27岁,博士研究生.
  • 基金资助:

    国家自然科学基金(批准号:29633020)资助课题

Theoretical Calculations of the Tautomeric Equilibrium in 3-X-2(1H)-Pyridones

ZOU Jian-Wei, LI Jiang-Bo, ZHU Long-Guan, YU Qing-Sen, LIN Rui-Sen   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310027, China
  • Received:1998-10-22 Online:1999-11-24 Published:1999-11-24

关键词: 取代基效应, 互变异构, 分子内氢键, 自洽反应场, 从头算

Abstract: The geometries of 3-X-2(1H)-pyridones(X=NO2, NH2, COOH) and their tautomers in the gas phase and DMSO solution(SCRF) have been obtained at HF/6-31G**and MP2/6-31G**levels. The influences of intramolecular hydrogen bond on the tautomeric equilibrium have also been investigated. In the gas phase, the calculated results show that the enol form is more stable than the keto form for 3-NO2-2(1H)-pyridone, and the keto?enol equilibrium shift right due to the formation of intramolecular hydrogen bond between 3-nitro and 2-hydroxyl group, while for the amino and carboxyl-derivatives, the keto forms are favored over the enol forms because of the stronger intermolecular hydrogen bonds in keto-tautomers. However, owing to the polarization effects of solvent, it can be predicted that the keto-tautomers are dominant for all of the title compounds in DMSO solution, which are in good agreement with the experimental results.

Key words: Substituent effect, Tautomerism, Intromolecular hydrogen bond, Self-consistent reaction field, Ab initio calculation

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