Date Written

2017

Document Type

Honors Paper

Degree Name

Biochemistry and Molecular Biology-BS

Department

Chemistry

Advisor

Dr. Robin Grote

First Committee Member

Dr. Dean Johnston

Second Committee Member

Dr. Stephanie Patridge

Keywords

oxadiazoles, heterocycles, bond length, product yield, biological activity, electron withdrawing group

Subject Categories

Heterocyclic Compounds | Medical Pharmacology | Medicinal and Pharmaceutical Chemistry | Organic Chemicals | Other Chemicals and Drugs | Other Pharmacy and Pharmaceutical Sciences | Pharmaceutical Preparations | Pharmaceutics and Drug Design | Polycyclic Compounds

Abstract

2,5-disubstituted 1,3,4-oxadiazoles are a class of organic compound that are widely used and successful in pharmaceutical chemistry because they demonstrate strong biological activity. They are part of a larger class of compound called heterocycles, which make up most pharmaceutical drugs today. When synthesizing the compounds, higher yield means higher reactivity of the compound, and this is important for pharmaceuticals that need to have a strong biological activity. Per past studies, electron withdrawing groups on the compound allow higher, product yields. Along with electron withdrawing group addition, the bond length from electron withdrawing group and its corresponding carbon is analyzed to look for positive correlation between high product yield and electron withdrawing group addition. The objective of this research is clarified by two phases: synthesis of 1,3,4-oxadiazoles with different electron withdrawing groups and analysis of yield and bond length. The conclusion of these phases demonstrates a trend between bond length and yield of the para oxadiazoles. As product yield increases, the bond length of the electron withdrawing group to carbon shortens. This trend is not observed in the ortho products because of other unknown factors, including steric hindrances that may limit the strength of the electron withdrawing group.