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The Nature and Kinetic Analysis of Carbon-Carbon Bond Fragmentation Reactions of Cation Radicals Derived from SET-Oxidation of Lignin Model Compounds

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Please use this identifier to cite or link to this item: http://hdl.handle.net/1928/12056

The Nature and Kinetic Analysis of Carbon-Carbon Bond Fragmentation Reactions of Cation Radicals Derived from SET-Oxidation of Lignin Model Compounds

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Title: The Nature and Kinetic Analysis of Carbon-Carbon Bond Fragmentation Reactions of Cation Radicals Derived from SET-Oxidation of Lignin Model Compounds
Author: Pimentel, Adam
Advisor(s): Dunaway-Mariano, Debra
Committee Member(s): Mariano, Patrick
Wang, Wei
Department: University of New Mexico. Dept. of Chemistry
Subject(s): Lignocellulosic
Biomass
Degree Level: Masters
Abstract: The lignin peroxidase promoted α−carbon β−carbon bond cleavage of two diastereomeric pairs of dimeric lignin model compounds were investigated to determine which structural units are more readily cleaved. These model compounds, β-1 (1,2-diaryl-1,3-propanediol) and β-O-4 (1-diaryl-2-aryloxy-1,3-propanediol), represent the most common structural units present in the plant cell wall polymer lignin. The lignin peroxidase catalyzed reaction mechanism was shown to parallel two mechanistically well understood systems, the cerric (IV) ammonium nitrate promoted chemical reacton, and the dicyannoanthracene promoted photochemical reaction, both of which proceed by a SET mechanism. Product profiles and kinetic rate constants were determined and compared for all four model compounds by HPLC and Stopped Flow kinetic techniques.
Graduation Date: December 2010
URI: http://hdl.handle.net/1928/12056

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