Degree Name

Master of Science (MS)

Semester of Degree Completion

Spring 2019

Thesis Director

Radu F. Semeniuc

Thesis Committee Member

Rebecca A. Peebles

Thesis Committee Member

Hongshan He

Thesis Committee Member

Gopal Periyannan

Thesis Committee Member

Zhiqing Yan

Abstract

Dinuclear copper complexes are significant synthetic targets due to their use as model compounds for the active sites of type 3 copper proteins like catechol oxidase. A distinct class of ligands used in these studies are built on a phenol core to witch various donor side-arms were appended at the 2 and 6 positions of the arene ring. In our quest to quantify the influence of electron donating or withdrawing groups attached to the central arene ring, we have designed a set of ligands that, upon coordination to copper(II) centers, would produce complexes of the general structure. During this research work, five new N60 heptadentate ligands have been prepared by the condensation of bis(pyrazolyl)ethanamine with different 2-hydroxy-isophthalic acids. These ligands react with copper(II) salts, forming bimetallic complexes, which were characterized by IR, UV-Vis and 1H-NMR spectroscopies. These complexes catalyze the oxidation of 3,5-di-tert-butylcatechol to the corresponding 3,5-di-tert-butyl quinone. The catalytic mechanism was investigated, and it was found that the oxidation reaction occurs via two different pathways, one involving molecular oxygen and the other the hydrogen peroxide byproduct.

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