Date of Award

Spring 4-5-2018

Document Type

Distinction Paper

Degree Name

Biochemistry and Molecular Biology-BS




Dr. Robin Grote

First Committee Member

Dr. John Tansey

Second Committee Member

Dr. David Robertson


Electron withdrawing, electron donating, oxadiazoles, dibromotriphenylphosphorane

Subject Categories

Organic Chemistry


The goal of this project was to determine the effects that electron withdrawing and electron donating substituents have on the synthesis of 1,3,4-oxadiazoles using a hydrazide starting material and dibromotriphenylphosphorane. This investigation involved the synthesis of hydrazide starting material followed by the synthesis of the oxadiazole with electron donating, withdrawing, or neutral substituents. Through this study, one neutral, three electron donating, two electron withdrawing substituents were investigated. Reactions were analyzed through nuclear magnetic resonance spectroscopy. Neutral electronegative substituents were deemed to be more successful through their percent yield and nuclear magnetic resonance spectroscopy data than both electron donating and withdrawing groups. Electron donating groups also produced more consistent and higher yields than electron donating substituents. Neither electron donating nor neutral substituents have enough statistical evidence to declare an affirmative trend, however, evidence from this study supports the hypothesis that electron withdrawing and neutral substituents are more ideal than electron donating substituents.