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Radical induced oxidative transforma...

Nicolaescu, A. Roxana.

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Radical induced oxidative transformations of N-heterocyclic compounds: Mechanistic and kinetic aspects.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Radical induced oxidative transformations of N-heterocyclic compounds: Mechanistic and kinetic aspects./
作者:	Nicolaescu, A. Roxana.
面頁冊數:	163 p.
附註:	Directors: Olaf Wiest; Prashant V. Kamat.
Contained By:	Dissertation Abstracts International65-05B.
標題:	Chemistry, Organic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3133137
ISBN:	9780496803774

Radical induced oxidative transformations of N-heterocyclic compounds: Mechanistic and kinetic aspects.
Nicolaescu, A. Roxana.

Radical induced oxidative transformations of N-heterocyclic compounds: Mechanistic and kinetic aspects. - 163 p.

Directors: Olaf Wiest; Prashant V. Kamat.

Thesis (Ph.D.)--University of Notre Dame, 2004.

The present study aims at understanding the fundamental aspects of the reaction mechanism of hydroxyl radicals with quinoline, 5- and 8-hydroxyquinoline, as model N-heteroaromatic compounds relevant in environmental chemistry. A multiprong approach has been applied to acquire mechanistic details, using pulse radiolysis and laser flash photolysis techniques, final product analysis and computational studies.

ISBN: 9780496803774Subjects--Topical Terms:

516206
Chemistry, Organic.

Radical induced oxidative transformations of N-heterocyclic compounds: Mechanistic and kinetic aspects.
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245 1 0 $a Radical induced oxidative transformations of N-heterocyclic compounds: Mechanistic and kinetic aspects.
300 $a 163 p.
500 $a Directors: Olaf Wiest; Prashant V. Kamat.
500 $a Source: Dissertation Abstracts International, Volume: 65-05, Section: B, page: 2421.
502 $a Thesis (Ph.D.)--University of Notre Dame, 2004.
520 $a The present study aims at understanding the fundamental aspects of the reaction mechanism of hydroxyl radicals with quinoline, 5- and 8-hydroxyquinoline, as model N-heteroaromatic compounds relevant in environmental chemistry. A multiprong approach has been applied to acquire mechanistic details, using pulse radiolysis and laser flash photolysis techniques, final product analysis and computational studies.
520 $a The •OH adds to the aromatic rings with diffusion controlled rates to form OH-adducts. The radical cation formed in the reactions with one electron oxidants undergoes fast hydrolysis to also form the OH-adducts. These OH-adducts undergo further transformations to form the final products. In the gamma radiolysis of the quinoline, hydroxylated products at all carbon positions but one, C2, were observed, along with higher molecular weight products (e.g., dimers). The reaction pathway for the attack of •OH at all carbon positions in quinoline were calculated both in gas phase and in solution using B3LYP/6-31G* method. The attack of •OH at C2 is different than the attack at all the other carbon positions: it involves the highest energetic barrier (5.1 kcal/mol). Therefore, the nature of the products is determined in the initial addition step of the reaction of •OH with quinoline, but the distribution of the final products depends on the chemistry of the OH-adducts. The hydroxyl group as the substituent on the benzene ring of the quinoline has a strong directing effect: the major product observed in the gamma radiolysis studies of the 5- and 8-hydroxyquinoline is quinoline-5,8-dione. However, computational results show that the •OH attacks at the ipso, ortho and para positions are energetically barrierless in solution.
520 $a The degradation of the N-heterocyclic compounds was investigated using the advanced oxidation technologies of sonolysis and photocatalysis. The lifetimes of the hydroxylated compounds were shorter than that of quinoline under the same conditions. The photocatalysis was much better at destroying and mineralizing the pollutants than the sonolysis. However total mineralization was achieved only under the simultaneous use of the two techniques.
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