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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (01): 71-74. 上一篇    下一篇

研究论文

以2-苯氧乙基为氮支链的[18]和[15]环系氮支套索冠醚的合成及其络合性能

刘淑芬*，刘春萍，徐强，孙琳，王志元，俞贵艳   

  1. (烟台师范学院化学与材料科学系 烟台 264025)
  • 收稿日期:2004-01-31 修回日期:2004-07-12 发布日期:2004-12-30
  • 通讯作者: 刘淑芬

Synthesis and Complexing Properties of New 18- and 15-Membered Ring N-Pivot Lariat Azacrown Ethers Containing N-(2-Phenoxyethyl)

LIU Shu-Fen*,LIU Chun-Ping,XU Qiang,SUN Lin
WANG Zhi-Yuan,YU Gui-Yan   

  1. (Department of Chemistry and Material Science, Yantai Teacher’s College, Yantai 264025)
  • Received:2004-01-31 Revised:2004-07-12 Published:2004-12-30
  • Contact: LIU Shu-Fen

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被引次数

2

以2-苯氧乙醇为起始剂, 合成了两种新型氮支套索冠醚: N-(2-苯氧乙基)单氮杂-18-冠-6 (18CE)与N-(2-苯氧乙基)单氮杂-15-冠-5 (15CE). 通过红外光谱、核磁共振氢谱和紫外光谱表征了新冠醚及其中间体的结构. 用电导滴定法研究了两冠醚与Na＋, K＋, Ag＋, NH4＋, Ni2＋, Cu2＋, Pb2＋和Co2＋在25 ℃的配位作用, 计算了1∶1配合物的稳定常数. 实验结果表明, 由于N-(2-苯氧乙基)引入氮杂冠醚环和参与配位, 18CE和15CE配合物的稳定常数分别比单氮杂-18-冠-6, N-(2-羟基乙基)单氮杂-18-冠-6, N-(2-甲氧基乙基)单氮杂-18-冠-6和单氮杂-15-冠-5, N-(2-甲氧乙基)单氮杂-15-冠-5, N-(2-甲氧乙基)单氮杂-15-冠-5的对应配合物明显提高. 配合物的稳定常数和紫外光谱皆提供了支链的苯氧基参与配位的信息.

关键词: 氮支套索冠醚, 合成, 电导滴定, 络合稳定常数

Using 2-phenoxyethanol as starting material, two new N-pivot lariat crown ethers were synthesized, N-(2-phenoxyethyl)monoaza-18-crown-6 (18CE) and N-(2-phenoxyethyl)monoaza-15-crown-5(15CE). The structures of the new crown ethers and the intermediate compounds were characterized by FTIR, 1H NMR and UV spectra. The coordination of Na＋, K＋, Ag＋, NH4＋, Ni2＋, Cu2＋, Pb2＋and Co2＋with two azacrown ethers was studied respectively by conductometric titration at 25 ℃. The stability constants for the 1∶1 coordination compounds were calculated. The results show that due to the induction and participation in complexing of the azacrown ether ring of N-(2-phenoxyethyl). The stability of the complexes has been improved more distinctly than that of homologue complexes of monoaza-18-crown-6, N-(2-hydroxyethyl)monoaza-18-crown-6, N-(2-methoxyethyl)monoaza-18-crown-6 and monoaza-15-crown-5, N-(2-hydroxyethyl)monoaza-15-crown-5, N-(2-methoxyethyl)monoaza-15-crown-5. The stability constants and UV spectra for the coordination compounds gave some evidences of pivot chain phenoxy group participating in complexing．

Key words: conductometric titration, stability constant, synthesis, N-pivot lariat crown ether