高等学校化学学报

高等学校化学学报 ›› 1995, Vol. 16 ›› Issue (5): 725.

• 论文 • 上一篇    下一篇

对称双吡咯甲烷的合成与分子内氢键的研究

陈清奇1, 王昌琦1, 程凌江1, 马金石1, 金声2   

  1. 1. 中国科学院感光化学研究所, 北京, 100101;
    2. 北京大学化学系
  • 收稿日期:1994-05-25 修回日期:1994-12-05 出版日期:1995-05-24 发布日期:1995-05-24
  • 通讯作者: 程凌江
  • 作者简介:陈清奇,男,31岁博士.
  • 基金资助:

    国家自然科学基金

Synthesis and Intramolecular Hydrogen Bonding of Symmetric Dipyrrylmethanes

CHEN Qing-Qi1, WANG Chang-Qi1, CHENG Ling-Jiang1, MA Jin-Shi1, JIN Sheng2   

  1. 1. Institute of Photographic Chemistry, Academia Sinica, Beijing, 100101;
    2. Department of Chemistry, Peking University, Beijing, 100871
  • Received:1994-05-25 Revised:1994-12-05 Online:1995-05-24 Published:1995-05-24

PDF (PC)

被引次数

1

摘要： 5-甲基吡咯-2-羧酸酯在磺酰氯、溴或四乙酸铅的作用下,生成相应的在5-甲基上含取代基的产物,后者不经分离便可自缩合得标题化合物。核磁共振氢谱研究和分子构象模拟计算表明,当3,3'位的取代基为甲酸(酯)基或乙酸(酯)基时,可形成3,3'位酯基与另一吡咯环上的氮氢之间的分子内氢键,而3,3'位是其它取代基,如乙酰基、丙酸(酯)基、丁酸(酯)基时不能形成类似的分子内氢键。

关键词: 双吡咯甲烷, 分子内氢键, 化学位移

Abstract: The title compounds were prepared by converting ethyl 5-methylpyrrole-2-car boxylates into corresponding 5-methyl substituted pyrroles oxydized by surfuryl chloride,bromine,or lead tetraacetate, and then self-condensed without separation and purification.The 1HNMR analysis and molecular conformation computation revealed that strong in tramolecular hydrogen bondings exist in dipyrrylmethane 4band 4c(3,3' substituents are for mate and acetate esters),while very weak or no intramolecular hydrogen bonding exists in other dipyrrylmethanes.

Key words: Dipyrrylmethane, Intramolecular hydrogen bonding, Chemical shift

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