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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (6): 564-568. 上一篇    下一篇

研究论文

苯甲酰氨基脲的合成及其阴离子识别

聂 丽*,a,b 李爱芳b 江云宝b

  

  1. (a皖西学院化学系 六安 237012)
    (b厦门大学化学化工学院化学系 现代分析科学教育部重点实验室 厦门 361005)

  • 投稿日期:2008-06-13 修回日期:2008-09-27 发布日期:2009-03-28
  • 通讯作者: 聂丽

Synthesis of N-Benzamidoureas and Its Anion Recognition

Nie, Li *,a,b Li, Aifang b Jiang, Yunbao b   

  1. (a Department of Chemistry, Wanxi College, Lu’an, Anhui 237012)
    (b Key Laboratory of Analytical Sciences, Ministry of Education, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005)
  • Received:2008-06-13 Revised:2008-09-27 Published:2009-03-28
  • Contact: Nie, Li

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被引次数

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设计合成了N-(取代苯甲酰氨基)脲衍生物(取代基＝p-OC2H5, H, p-Cl) 1～3, 应用吸收光谱法考察了受体分子与阴离子如 , F－, 等的相互作用, 考察了取代基对受体分子与阴离子亲合力和结合选择性的调控或改善能力. 结果表明, 该类受体分子与阴离子通过氢键形成阴离子配合物, 乙腈中受体分子1对F－表现出极高的响应选择性. Job作图法表明1与F－的结合计量比为1∶1, 1H NMR滴定结果为受体分子与阴离子间的氢键作用本质提供了直接证据, 初步探讨了F－响应选择性的原因.

关键词: 苯甲酰氨基脲, 阴离子识别, 氢键, F－

Three N-(substituted-benzamido)urea-based receptors (substituent＝p-OC2H5, H, p-Cl) 1～3, were designed and synthesized. Their interactions with anions such as , F－, , , Cl－ and Br－ in acetonitrile were investigated by using absorption spectroscopy. 1H NMR titrations and Job plots confirming that 1∶1 hydrogen-bonding complexes were formed between the receptors and anions. Results showed that varying substituent could efficiently tune the hydrogen bonding interaction with anions and modulate the selectivity and sensitivity to anion recognition. Receptor 1 bearing an electron-donating substituent showed a highly selective recognition of a fluoride anion, which may result from the formation of an intramolecular seven-membered ring hydrogen bond in the receptor molecule that affords a suitable arrangement of the anion binding sites matching well for a fluoride anion.

Key words: N-benzamidourea, anion recognition, hydrogen bonding, fluoride