Date Written

2017

Document Type

Honors Paper

Degree Name

Biochemistry and Molecular Biology-BS

Department

Chemistry

Advisor

Dr. Robin Grote

First Committee Member

Dr. Robin Grote

Second Committee Member

Dr. Carrigan Hayes

Third Committee Member

Dr. Karen Steigman

Keywords

oxadiazole, yield, electron-donating, heterocycle

Subject Categories

Chemicals and Drugs | Medicinal and Pharmaceutical Chemistry | Organic Chemicals

Abstract

This investigation focused on determining if there was a relationship between electron donating group substituent strength and resulting percent yield values of the 1,3,4-oxadiazole product. The data obtained from this investigation aimed to help chemists better understand the reactivity of the 1,3,4-oxadiazole because of its importance in the realm of drug design and development. In order to accomplish this, electron donating groups with varying pKa values were placed on the 1,3,4-oxadiazole and the resulting percent yields were analyzed for possible trends. The substituents used represented both resonance donating and inductively donating groups and were placed in both ortho and para positions to demonstrate possible steric effects. A direct correlation between electron donating strength and percent yield was not found, but the data did show lesser yield values when compared to similar reactions involving electron withdrawing groups.

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