首页> 外文学位 >Preparation and study of 8-hydroxyquinoline derivatives: 5-Carbonyl-8-hydroxyquinoline nitrogen-oxides and spin-labeled 8-hydroxyquinolines.
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Preparation and study of 8-hydroxyquinoline derivatives: 5-Carbonyl-8-hydroxyquinoline nitrogen-oxides and spin-labeled 8-hydroxyquinolines.

机译:8-羟基喹啉衍生物的制备和研究:5-羰基-8-羟基喹啉氮氧化物和自旋标记的8-羟基喹啉。

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摘要

Two types of chelating agents were prepared: 5-carbonyl-8-hydroxyquinoline N-oxides and spin-labeled 8-hydroxyquinolines. The formyl, acetyl, and benzoyl N-oxide derivatives were compared to the corresponding 8-hydroxyquinoline derivatives. Two spin-labeled reagents were prepared: compound A, 2-(8-hydroxyquinol-5-yl-N-oxide)-4,4,5,5-tetramethylimidazoline 3-oxide 1-oxyl, and compound B, the corresponding 8-hydroxyquinoline derivative. Two other compounds were prepared and isolated: ;All chelating agents were tested for chelating ability with eight metal ions: Cu(II), Ni(II), Mn(II), Co(II), Pb(II), Zn(II), Fe(III), and Al(III). Two testing procedures were used. The pH range was 6-8.;The carbonyl derivatives were studied by IR, UV, NMR, and TLC. The differences observed between the 5-carbonyl-8-hydroxyquinoline N-oxides and the corresponding 8-hydroxyquinoline derivatives were primarily the result of hydrogen bonding. In the N-oxides, a strong intra-molecular chelation-type hydrogen bond is formed between the phenolic hydrogen and the N-oxide oxygen. Both intra- and inter-molecular hydrogen bonds are formed in the 8-hydroxyquinolines. In addition, evidence was observed for possible hydrogen bond formation between the carbonyl oxygen and the peri hydrogen. The spectra--NMR, UV, and IR--of 8-hydroxyquinoline, 8-hydroxyquinoline N-oxide, and their carbonyl derivatives are shown in the thesis.;The radicals were studied by IR, UV-VIS, ESR, and TLC. Separation and purification of the radicals were done by chromatographic methods. Flash chromatography employing silica gel and eluant mixtures of methanol and chloroform was used to isolate and purify compound A. However, the characteristic tailing of 8-hydroxyquinoline compounds on silica gel hindered the separation, and compound B was not isolated. In the chelation testing, both compounds A and B reacted with Cu(II) and Fe(III). The reaction products were not isolated. Linear absorbance-concentration curves were observed in both ESR and UV-VIS. The isolated dihydroxylamine radical precursors were studied by IR and NMR. Spectra for IR, NMR, ESR, and UV-VIS are shown in the thesis.
机译:制备了两种类型的螯合剂:5-羰基-8-羟基喹啉N-氧化物和自旋标记的8-羟基喹啉。将甲酰基,乙酰基和苯甲酰基N-氧化物衍生物与相应的8-羟基喹啉衍生物进行比较。制备了两种自旋标记试剂:化合物A,2-(8-羟基喹啉-5-基-N-氧化物)-4,4,5,5-四甲基咪唑啉3-氧化物1-氧基和化合物B,相应的8 -羟基喹啉衍生物。制备并分离了另外两种化合物:;测试了所有螯合剂与八种金属离子的螯合能力:Cu(II),Ni(II),Mn(II),Co(II),Pb(II),Zn(II ),Fe(III)和Al(III)。使用了两种测试程序。 pH范围为6-8。通过IR,UV,NMR和TLC研究羰基衍生物。在5-羰基-8-羟基喹啉N-氧化物和相应的8-羟基喹啉衍生物之间观察到的差异主要是氢键的结果。在N-氧化物中,在酚氢和N-氧化物氧之间形成强分子内螯合型氢键。分子内和分子间氢键均在8-羟基喹啉中形成。另外,观察到在羰基氧和周围氢之间可能形成氢键的证据。给出了8-羟基喹啉,8-羟基喹啉N-氧化物及其羰基衍生物的NMR,UV和IR光谱。通过IR,UV-VIS,ESR和TLC对自由基进行了研究。 。自由基的分离和纯化通过色谱法进行。使用硅胶的快速色谱法和甲醇和氯仿的洗脱液混合物分离和纯化化合物A。但是,8-羟基喹啉化合物在硅胶上的特征性拖尾阻碍了分离,并且未分离出化合物B。在螯合测试中,化合物A和B均与Cu(II)和Fe(III)反应。未分离反应产物。在ESR和UV-VIS中均观察到线性吸光度-浓度曲线。通过IR和NMR研究分离的二羟胺自由基前体。论文给出了红外,核磁共振,ESR和紫外可见光谱。

著录项

  • 作者

    Oakdale, Joyce E.;

  • 作者单位

    Loyola University Chicago.;

  • 授予单位 Loyola University Chicago.;
  • 学科 Chemistry Analytical.
  • 学位 Ph.D.
  • 年度 1988
  • 页码 232 p.
  • 总页数 232
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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