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硫杂杯-1,3-2,4-氮杂双冠醚的合成与氨基酸配合性能

杨发福1, 黄翠玉1, 赵夏1, 郑思宁1, 彭奇2   

    1. 福建师范大学化学与材料学院, 福州 350007;
    2. 中国科学院福建物质结构研究所, 结构化学国家重点实验室, 福州 350022
  • 收稿日期:2006-05-29 修回日期:1900-01-01 出版日期:2007-05-10 发布日期:2007-05-10
  • 通讯作者: 杨发福

Synthesis and Amino Acids Complexation Properties of Thiacalix-1,3-2,4-aza-bis-crowns

YANG Fa-Fu1*, HUANG Cui-Yu1, ZHAO Xia1, ZHENG Si-Ning1, PENG Qi2   

    1. College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007, China;
    2. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
  • Received:2006-05-29 Revised:1900-01-01 Online:2007-05-10 Published:2007-05-10
  • Contact: YANG Fa-Fu

摘要: 对叔丁基硫杂杯四酰肼衍生物(2)与邻苯二甲醛发生分子内1+2缩合反应, 合成了首例1,3-交替构象的硫杂杯-1,3-2,4-氮杂双冠醚(3), 产率为65%. 其结构经元素分析、质谱、核磁共振谱等表征证实. 用UV-Vis光谱法和1H NMR谱研究了化合物3与系列α-氨基酸的识别配合性能, 并计算出其配合常数. 结果表明, 主体分子3对所测试的α-氨基酸有较好的配合作用, 主客体分子形成1∶1的配合物.

关键词: 硫杂杯双冠醚, 氮杂, 氨基酸, 配合

Abstract: Thiacalixarene is an interesting novel member of the calixarene family. Thiacalixcrowns were paid much attention due to their particular structures and excellent complexation capabilities. In this paper, by reacting p-tert-butylthiacalixarene tetrahydrazide derivative 2 with o-phthalaldehyde, the first example of thiacalix-1,3-2,4-aza-bis-crowns with 1,3-alternate conformation was prepared with “1+2” condensation mode in a 65% yield. Its structure was characterized by elemental analysis, ESI-MS, 1H NMR spectrum. Its complexation properties for series of α-amino acids were studied via UV-Vis and 1H NMR spectra. Their high complexing constants suggest novel thiacalixbiscrown 3 possessed excellent comple-xation abilities for tested amino acids. The correlation coefficients and the 1H NMR spectra change of comple-xation experiments indicate that compound 3 formed 1∶1 stoichiometric complex with amino acids.

Key words: Thiacalixbiscrown, Aza, Amino acid, Complexation

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