Studies Toward Provenance Determination For Indigo Dyes, Erin Kibby

Undergraduate Honors Thesis Projects

Species of indigo-producing plants have been used to color textiles for thousands of years all over the globe. Natural indigo-producing species have historically been harvested in regions of Asia, North Africa, and North and South America. This study is an exploration of methods that can be used to determine the provenance (origin) of the indigo dye in a textile through the extraction and isolation of indigoids, flavonoids, and other compounds from the natural dyestuff. There is no accepted method of extracting flavonoids from indigo-dyed textiles specifically, and there is little investigation of the regionally different species. If a method is …

Antibacterial Activity, Structure-Activity Relationships, And Scale-Up Reaction Of 1,3,4-Oxadiazoles, Olivia Marie Smith

Undergraduate Honors Thesis Projects

Oxadiazoles are compounds in the field of organic chemistry that have been gathering interest in the medicinal chemistry and microbiology communities for their biological properties, which range from anti-inflammatory agents, to chemotherapy drugs, to antibiotics. The synthesis of oxadiazoles can be difficult due to the expensive and complex nature of the techniques used as well as the volatile reagents and elevated temperatures that are often required in organic synthesis. The Grote lab has recently developed a new method for the synthesis of 1,3,4-oxadiazoles under mild conditions. The goals of this thesis were thus twofold: to develop a viable scale-up procedure …

Mechanistic Studies And Derivative Effects In 1, 3, 4- Oxadiazole Synthesis Via Cyclodehydration Reactions, Evan Huggins

Undergraduate Honors Thesis Projects

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 …

Investigating The Synthesis Of 1,3,4-Oxadiazoles Via A Novel Two-Step-One-Pot Cyclodehydration Reaction, Brittney Sowers

Undergraduate Honors Thesis Projects

The given research will investigate synthetic strategies and differential functionalization of 1,3,4- oxadiazoles in hopes of obtaining moderate to high yields. Particularly, the effects of electron withdrawing on oxadiazoles will reveal more information about possible mechanistic details and reaction optimization.

The research in this report is a part of a lager research effort being investigated by Dr. Robin Grote. This research is ongoing and has evolved from its start in the Grote Lab. Previously, the Grote Lab has focused on the formation of a patented heterocycle that contained an amino-pyrazine functional group. Currently, our research has shifted focus to the …

Synthesis Of Oxadiazoles And Examination Of Steric Effects In A Cyclodehydration Reaction, Norah Young

Undergraduate Honors Thesis Projects

The objective of this project is to develop a general substrate scope by testing various steric and electronic effects. This is pursued by developing triphenylphosphine dibromide (PPh3Br2) as an effective cyclodehydration reagent for use with a variety of hydrazides and sterically and electronically different benzoic acids. The two phases of the experiment include assessing yield through a cyclodehydration reaction and comparing that yield to the steric hindrance and molecular structure recorded in different databases. The cyclodehydration reaction uses ortho-substituted benzoic acid with store bought PPh3Br2, and compares those yields to the use of a two step-one pot reaction in place …

Development And Characterization Of A Paper Based Analytical Device For Heparin Quantification, Carolanne Norris

Undergraduate Honors Thesis Projects

Paper-based analytical devices (PAD) have gained popularity in the past ten to fifteen years due to many favorable mechanical properties.1 They have largely been used to analyze small ionic species, such as Na+ and Li+, but little research has been done on their capability of to analyze large polyionic species, for instance the highly sulfonated polysaccharide heparin.2,3 This study explores adaptation of a traditional optode design to a low cost PAD that employs a smartphone as a detector. Throughout the study variables, such as membrane composition, pH, volume of solution, time, addition of a polymer, use of different cell phone …

Imidazolium Salts As Reaction Media For The Preparation Of Metal Halide Cluster Networks, Stephanie K. Gnewuch

Undergraduate Honors Thesis Projects

This study investigated two different schemes of imidazolium and carboxylate salts to assess their use in preparing metal halide cluster networks. The first scheme used salts of 1-ethyl-3-methylimidazolium [EMIM]⁺ and 1-butyl-3-methylimidazolium [BMIM]⁺ as the cations and benzene-1,3,5-tricarboxylate [TMA]-, benzene 1,3-dicarboxylate [IPA]-, and benzene-1,4-dicarboxylate [TPA]- as the anions. The anions are commonly used in porous inorganic materials synthesis, as the size of the cation has been shown to often impact the final structure of the materials. The anions are common bridging ligands used to create network solids. The second scheme used 1,3-dimethylimidazolium triflate [DMIM]⁺ [OTf]^- and sodium …

Transition Metal Catalysis And The Synthesis Of Biologically Interesting Heterocycles: A Study Of Gold-Catalyzed Intermolecular Cyclization And Palladium-Catalyzed Suzuki Cross-Coupling, Alexandria E. Weber

Undergraduate Honors Thesis Projects

Two methods of transition metal catalysis were investigated as a means to synthesize biologically interesting heterocyclic molecules. The gold-catalyzed intermolecular cyclization of allenes and 1,3-dipoles was first explored. An allene, ethyl-3-hexyl-3,4-pentadienoate was subjected to a combination of one of five 1,3-dipoles ((Z)-N-benzylidenemethanamine oxide, 1-benzylidene-3-oxopyrazolidin-1-ium-2-ide, (Z)-N-benzylidenebenzenamine oxide, (E)-N-benzylidenebenylamine, and (E)-N-Benzylidene-4-methoxybenzenamine) and one of three gold catalysts (1,3-bis(2,6-di-isopropylphenyl)imidazole-2-ylidenegold(I)chloride, chlorotriphenyl-phosphinegold(I), and gold(III) chloride). No heterocyclic product resulted from these catalytic reactions. The palladium-catalyzed Suzuki cross-coupling reaction of a 1,3,4-oxadiazole (3-(5-(4-(bromo)phenyl)-1,3,4-oxadiazol-2-yl)pyrazine-2-amine) with phenyl boronic pinacol ester was then explored, varying whether the 1,3,4-oxadiazole was unprotected or …

Investigating The Synthesis Of Heterocycles Via Gold Catalyzed Cyclizations And Cyclo-Dehydrating Reactions, Katherine L. Childers

Undergraduate Honors Thesis Projects

The goal of this project was to study novel synthetic procedures for heterocycles. This was achieved through a two-part investigation. In the first part, a variety of conditions for the gold catalyzed cyclization of allenes were studied. This work was focused on the lesser studied intermolecular reactions of allenes. A variety of allenes were synthesized, and then reacted with 1,3-dipoles and a gold catalyst. These reactions were determined to be unsuccessful through the analysis of nuclear magnetic resonance spectroscopy data. In the second part of this study, the synthesis of 1,3,4-oxadiazoles was investigated. Several cited procedures were examined to determine …