Date of Award

4-12-2019

Document Type

Honors Paper

Degree Name

Biochemistry and Molecular Biology-BS

Department

Chemistry

Advisor

Robin Grote, Ph.D.

First Committee Member

Robin Grote, Ph.D.

Second Committee Member

Carrigan Hayes, Ph.D.

Third Committee Member

Erica Van Dop

Keywords

1, 3, 4-oxadiazole, mechanism, derivative effects, dibromotriphenylphosphorane, Molecular Mechanics 2, Parameterized Model 3

Subject Categories

Heterocyclic Compounds | Medicinal-Pharmaceutical Chemistry | Organic Chemicals | Organic Chemistry | Pharmaceutical Preparations | Physical Chemistry

Abstract

In the world of pharmaceutical synthesis, research to combat foreign pathogens is always necessary. Scientists have been exploring different methods in order to synthesize the most effective compounds in antibacterial, anticancer, anti-inflammatory, and many other treatments. A key component within these versatile compounds are 1,3,4-oxadiazoles. Current methods to synthesize these compounds are inefficient. This research seeks to improve oxadiazole synthesis; however, the mechanism of this reaction is unknown. The goal of this project was to study the mechanistic pathway in the discovered, one-pot cyclodehydration synthesis of 1,3,4-oxadiazoles. In the first part of this study, a diacylhydrazine intermediate was proposed. This commercially available diacylhydrazine was submitted to reaction conditions to test this mechanistic hypothesis. Finally, the laboratory data was combined with thermodynamic computational data in order to observe the Gibbs free energies and equilibrium constants of this reaction. These values can provide key insight into the electron donating and electron withdrawing groups effects on the mechanism of this reaction. This was completed by utilizing various approaches including Molecular Mechanics 2 (MM2) in ChemBio 3D, and PM3 within the Spartan 16 program. Bond dissociation enthalpies were also consulted in order to provide a general investigation of the proposed mechanism.

Available for download on Sunday, April 11, 2021

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