物理化学学报 >> 2007, Vol. 23 >> Issue (07): 1018-1024.doi: 10.1016/S1872-1508(07)60057-6

研究论文 上一篇    下一篇

尿素及硫脲与羰基化合物间的氢键相互作用

郑文锐; 傅尧; 刘磊; 郭庆祥   

  1. 中国科学技术大学化学系, 合肥 230026
  • 收稿日期:2006-12-21 修回日期:2007-03-29 发布日期:2007-07-03
  • 通讯作者: 傅尧 E-mail:fuyao@ustc.edu.cn

Hydrogen Bonding Interaction between Ureas or Thioureas and Carbonyl Compounds

ZHENG Wen-Rui; FU Yao; LIU Lei; GUO Qing-Xiang   

  1. Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China
  • Received:2006-12-21 Revised:2007-03-29 Published:2007-07-03
  • Contact: FU Yao E-mail:fuyao@ustc.edu.cn

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摘要： 利用量子化学二级微扰理论方法对尿素及硫脲衍生物与羰基化合物之间的氢键复合物进行了研究, 在自然键轨道分析基础上进一步揭示了氢键本质并研究了取代基效应. 结果表明, 羰基化合物中供电子基和共轭基, 尿素及硫脲中的吸电子基和共轭基均有利于氢键的形成. 结合尿素与硫脲的催化反应过程, 讨论了氢键复合物两种可能的顺反异构并分析比较了顺反式构象异构体的稳定能大小.

关键词: 氢键, 羰基化合物, 顺反异构, 尿素, 硫脲

Abstract: The hydrogen bonding interactions between ureas or thioureas and different carbonyl compounds were studied using the Moller-Plesset perturbation theory (MP2) method. The natural bond orbital analysis further disclosed the essence of the hydrogen bonding interaction. In addition, the substituent effects were investigated and the results indicated that both the electron-withdrawing groups on ureas (thioureas) and electron-donating groups on carbonyl compounds can facilitate the hydrogen bonding formation. Two possible hydrogen bonding complex conformations, cis and trans, were discussed and the energy gaps between themwere analyzed, in combination with the catalytic reactions.

Key words: Hydrogen bond, Carbonyl compound, cis-trans isomerization, Urea, Thiourea