Radical-Induced Oxidative Transformation of Quinoline

A. Roxana Niclolaescu; Olaf Wiest; Prashant V. Kamat

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Radical-Induced Oxidative Transformation of Quinoline

机译：自由基诱导的喹啉氧化转化

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The primary events of the oxidative transformation of quinoline, an environmental pollutant, by different radicals have been investigated using pulse radiolysis. The hydroxyl radical reacts by adding to both pyridine and benzene rings of quinoline to form the OH-adducts. On the other hand, SO_4~(·-) oxidizes the quinoline to its radical cation, which further undergoes hydrolysis to yield the OH-adducts. The possibility of the quinoline radical cation to undergo hydrolysis has been independently verified by generating the radical cation under laser induced photoinonization conditions. The quinoline radical cation produced in acetonitrile shows high reactivity toward water. The rate for ·OH reaction is greater (k = 1.0 * 10~(10) M~(-1) s~(-1)) than that found for SO_4~(·-) reaction (k = 3.5 * 10~9M~(-1) s~(-1)). With oxidation potential at 1.87 V vs NHE, quinoline is nonreactive toward ·Ns radicals and less reactive toward ·O~- radicals (k = 3.2 * 10~8 M~(-1)s~(-1)). The mechanistic understanding of the primary oxidation pathway of quinoline will aid in designing strategies for the abatement of pollutants containing nitrogen heterocycles.

机译：使用脉冲辐射分解研究了喹啉（一种环境污染物）被不同自由基氧化转化的主要事件。羟基自由基通过加到喹啉的吡啶环和苯环上反应形成OH加合物。另一方面，SO_4〜（·-）将喹啉氧化成其自由基阳离子，然后进一步水解产生OH加合物。喹啉自由基阳离子发生水解的可能性已通过在激光诱导的光电离条件下产生自由基阳离子而得到独立验证。乙腈中产生的喹啉自由基阳离子显示出对水的高反应活性。 ·OH反应的速率（k = 1.0 * 10〜（10）M〜（-1）s〜（-1））比SO_4〜（·-）反应的速率（k = 3.5 * 10〜9M 〜（-1）s〜（-1））。相对于NHE，氧化电位为1.87 V，喹啉对·Ns自由基无反应，而对·O〜-自由基则反应性较低（k = 3.2 * 10〜8 M〜（-1）s〜（-1））。对喹啉主要氧化途径的机理理解将有助于设计减少含氮杂环污染物的策略。

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《The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory》 |2003年第3期|共7页
作者
A. Roxana Niclolaescu; Olaf Wiest; Prashant V. Kamat;
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中图分类物理化学（理论化学）、化学物理学;
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1. Radical-Induced Oxidative Transformation of Quinoline [J] . A. Roxana Niclolaescu, Olaf Wiest, Prashant V. Kamat The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2003,第3期

机译：自由基诱导的喹啉氧化转化
2. Isothiazolo-fused quinoline analogues: Synthesis of isothiazolo [5,4-b] quinolines and their oxidation products, 3[2H]-one-1, 1-dioxideisothiazolo [5,4-b] quinolines from 2-chloro-3-formylquinolines [J] . Srivastava A, Chandra A, Singh RM Indian Journal of Chemistry, Section B. Organic Including Medicinal . 2007,第2期

机译：异噻唑啉并稠的喹啉类似物：由2-氯-3-甲酰基喹啉合成异噻唑并[5,4-b]喹啉及其氧化产物，3 [2H] -one-1，1-dioxideisothiazolo [5,4-b]喹啉。
3. Isothiazolo-fused quinoline analogues:Synthesis of isothiazolo [5,4-b] quinolines and their oxidation products,3[2H]-one-1,1-dioxideisothiazolo [5,4-b] quinolines from 2-chloro-3-formylquinolines [J] . A Srivastava, Atish Chandra, R M Singh Indian Journal of Chemistry, Section B. Organic Including Medicinal . 2007,第2期

机译：异噻唑并稠喹啉类似物：由2-氯-3-甲酰基喹啉合成异噻唑并[5,4-b]喹啉及其氧化产物，3 [2H] -one-1,1-dioxideisothiazolo [5,4-b]喹啉。
4. Mechanistic studies of hydroxyl radical-induced catalytic wet oxidation of dyehouse effluents at atmospheric pressure [C] . Dong-Keun Lee, Dul-Sun Kim, Sung-Chul Kim 3rd International Symposium on Reaction Kinetics and the Development and Operation of Catalytic Processes, Apr 22-25, 2001, Oostende, Belgium . 2001

机译：大气压下羟自由基诱导的印染废水催化湿式氧化的机理研究
5. Decomposition of hydrogen peroxide and oxidation of quinoline in the presence of iron oxides. [D] . Wang, Heng-Chuan Ann. 1996

机译：过氧化氢的分解和喹啉在氧化铁存在下的氧化。
6. Toluene Dioxygenase-Catalyzed cis-Dihydroxylation of Quinolines: A Molecular Docking Study and Chemoenzymatic Synthesis of Quinoline Arene Oxides [O] . Derek R. Boyd, Narain D. Sharma, Pui L. Loke, 2020

机译：喹啉二氧化碳酶催化顺式二羟基化：喹啉芳烃氧化物的分子对接研究和化学酶合成
7. Studies on the reaction of quinazoline 3-oxide with ketone. The transformation of quinazoline 3-oxide into quinoline derivatives. [O] . TAKEO HIGASHINO, KIYOSHI SUZUKI, EISAKU HAYASHI 1975

机译：喹唑啉3-氧化物与酮的反应研究。喹唑啉3-氧化物转化为喹啉衍生物。
8. Biotransformation of Quinoline and Methylquinolines in Anoxic Freshwater Sediment [R] . Liu, S. M., Jones, W. J., Rogers, J. E. 1994

机译：喹啉和甲基喹啉在缺氧淡水沉积物中的生物转化

Radical-Induced Oxidative Transformation of Quinoline

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