Organic Chemistry Commons^™

Chemistry In Medicine, Olivia Visaggio, Alyssa Bondi, Matthew Gillingham, Hailey Loughlin

Student Research Poster Presentations 2020

The chemistry behind medicine is important and necessary to study many different drugs and their effects. In this project, we focused on the chemical composition and mechanisms of various drugs. The drugs we focused on include Opioids, NSAIDs, and other medications, such as Benzodiazepines and antibiotics. For each drug, we provided its structure as well as the functional groups, which include a part of a molecule that is recognized based on its arrangement of atoms. Organic Chemistry provides individuals with an understanding of various organic compounds, and this field of study is important as it explains the ways in which …

Electrolytic Oxidative Coupling Of Alcohols With Aldehydes To Form Esters, Katherine L. Verboom

Honors College Theses

There are copious amounts of naturally occurring and synthetic esters known that have a wide range of applications in industry to produce fine chemicals. Traditional methods of ester synthesis involve a reaction between a carboxylic acid and an alcohol in the presence of a Bronsted acid catalyst. The primary objective of this research project was to carry out the ester synthesis using the electrochemical coupling of aldehydes with alcohols instead of with a Bronsted acid catalyst because the electrochemical coupling would be an all-around better alternative of ester synthesis than the traditional method of using the catalyst. Electrochemistry has long …

Synthesis Of Bio-Based Polymer Products, Joshua Sukie

Williams Honors College, Honors Research Projects

The project covers the synthesis of two bio-based polymers. One aspect of the research investigates the synthesis of materials for use in vegetable oil-based UV-curable coating, and the subsequent polymerization of the materials into a coating film. The second aspect of the research follows the synthesis of a functionalized cellulose material for use as a reinforcer in a vegetable oil-based composite. Both products are subsequently analyzed by various methods.

Hypervalent Iodine Compounds With Carboxylate And Tetrazolate Ligands, Avichal Vaish

Chemistry Theses and Dissertations

In modern organic chemistry, hypervalent (HV) iodine(III) compounds are frequently used as oxidizing agents but application of λ³-iodanes in polymer and material chemistry is still underexplored. This dissertation describes the preparation of dynamic and self-healing materials by employing ligand exchange reactions involving HV iodine(III) compounds of the type ArIL₂ (Ar = Aryl, L = ligand, e.g., carboxylate or (pseudo)halide). These compounds can undergo ligand exchange reactions in presence of nucleophiles (Nu^-) to form ArINu₂. Diacetoxyiodo benzene was successfully employed as a crosslinker to prepare dynamic and self-healing gels derived from carboxylate-containing polymers. Furthermore, …

Cell-Trappable Chemiluminescent Probes For Monitoring Hydrogen Sulfide In Living Cells, Briley Bezner

Chemistry Theses and Dissertations

Hydrogen sulfide (H2S) is an important biological signaling molecule that has been recognized alongside nitric oxide and carbon monoxide as being a small gasotransmitter that is enzymatically produced and impacts multiple physiological functions. To detect hydrogen sulfide, there has been a focus on developing fluorescent probes to target particular analytes; however, fluorescent probes lack sensitivity and depth penetration due to background autofluorescence and light scattering. Chemiluminescence does not require light excitation, which greatly reduces the amount of autofluorescence and photoactivation.

In order to detect hydrogen sulfide in living systems with high sensitivity, a series of sterically stabilized 1,2-dioxetane chemiluminescent reduction-reaction …

Hierarchical Conjugated Polymer Systems Prepared By Controlled Chain-Growth Polymerization, Chunwa Peter Kei

LSU Doctoral Dissertations

π-Conjugated polymer materials may have a significant economic impact on society by providing means for designing affordable, flexible, and portable organic electronic devices. Their successful commercialization will depend on major scientific advancements, which will challenge human society to seek out ever more detailed and fundamental processes to command. Controlled polymerization affords such a power; allowing for the design of meticulous and precisely defined systems granting detailed insight into structure-property relationships in the polymer materials and bettering understanding of novel physical phenomena.

This dissertation primarily focuses on development and preparation of well-defined hierarchically organized macromolecular systems. The novel chain-growth polymerization methodologies …

Double-Click Enables Synthesis Of Chemical Libraries For Drug Discovery, Joseph J. Topczewski, En Chih Liu

Chemistry Faculty Research & Creative Works

No abstract provided.

The Roundtable Of Scientific Communication: From Classroom To Course Creation, Back To Classroom And Beyond, Sean P. Hickey

LSU New Orleans Theses and Dissertations

This research encompasses many aspects of chemical education research including curriculum and pedagogical changes to the freshman and sophomore courses. Curriculum changes included the addition of recitations to the general chemistry and organic chemistry lectures and the creation of four new classes, CHEM 1001, 1002, 3091, and 3092. The addition of recitations was not limited to but was focused on improving DFW rates for these courses.

CHEM 3091 and 3092 are chemistry internship and undergraduate teaching assistant classes. These courses were necessary to offer outside internship opportunities and training for undergraduate teaching assistants, respectively. CHEM 1001 and 1002 are chemistry …

Molecular Machines: Synthesis, Modeling, And Applications, Syd Kotar

Student Scholar Symposium Abstracts and Posters

While some of the smallest, most useful machines known to science are the biological molecules that keep living organisms alive, there is a growing advancement of the creation of artificial molecules that have the same function and are more efficient. Molecular machines were invented in 1983 when scientists in France created a machine formed of two interlinked molecular rings. In 2016, the Nobel prize in chemistry was awarded to Feringa, Stoddart, and Sauvage who finally documented molecular machines and put them into energy‐filled states in which their movements could be controlled. From this, molecular machines became known as a group …

A Stereospecific Pd-Catalyzed Suzuki Cross-Coupling Reaction And A Statistical Study Of The Ligand's Role In Stereoselection, Shibin Zhao

Dissertations, Theses, and Capstone Projects

The development of palladium-catalyzed carbon-carbon cross-coupling reactions has profoundly influenced the manner through which we approach the synthesis of complex organic molecules. Among established cross-coupling reactions, which include Kumada, Negishi, and Stille reactions, the Suzuki cross-coupling reaction exhibits particularly wide functional group compatibility, while employing non-toxic, air-stable organoboron nucleophiles. Conventional studies of Pd-catalyzed Suzuki cross-coupling reactions have focused on C(sp²)-C(sp²) cross-coupling reactions, which result in the formation of planar products. Conceptually, the use of C(sp³) (secondary) nucleophiles would enable the reliable manipulation of organic molecules in three dimensions. However, this process has not been …

Design And Synthesis Of Circadian Clock Modulators And The Study Of Lov Domain Protein Lkp2 In Arabidosis Thaliana And Brassica Rapa, Aditi Nagar

Chemistry Theses and Dissertations

Circadian rhythms are self-autonomous endogenous clocks synchronized with the rotation of the Earth. With the Earth’s rotation and revolution on its axis, the internal clock undergoes oscillation in the period of ~24 hour and governs day to day activities in most organisms. In humans, it regulates the day to day physiological activities. Today’s modern lifestyle has an impact on health: shift work, jet lag, and irregular eating habits contribute to the misalignment of the endogenous circadian oscillator, thereby, increasing the risk of many metabolic disorders including diabetes, irregular blood pressure, sleep disorders, obesity, depression, and cancer. The primary goal of …

Rearrangements Of Fluorinated Cyclopropylamines As A Novel Approach Toward Fluoroalkene-Based Peptidomimetics, Igor Mezentsev, Vera Zaborova

The International Student Science Fair 2018

Organofluorine molecules have been widely applied in various research fields because of the unique properties of fluorine atoms. One type of fluorinated compounds is fluoroalkene-based peptidomimetics which are structurally similar to amide-containing compounds. They have been prepared to improve the pharmaceutical properties such as bioactivity, target specificity, and metabolic stability of the bioactive amides.

We suggested a new way of synthesizing fluoroalkene-based peptidomimetics through 2-fluoro-2-halocyclopropylamines, which provides an effective way toward fluoroalkene-based peptidomimetics with increased functional group tolerance and possibility of convergent synthesis.

Steric Effects Of Alkyl Ammonium Salts On The Combustion Of Exchanged Smectite Clays, Celeste A. Keith

Electronic Theses and Dissertations

Bomb calorimetry was explored as a new method for determining the cation exchange capacity (CEC) of clays. Smectite clays were modified with several alkyl ammonium salts varying in number of carbons and the spatial orientation of the carbons about the central nitrogen atom. The clays used, standards purchased from the Source Clay Repository, have CECs of 44, 80, 88, and 120 meq/100 g. Theoretically, the combustion energy of the organo-clays should be approximately the same for each salt. Any differences in energy would be due to the different structures of the salts and how they are oriented in the interlamellar …

Multi-Reference Systems In Chemistry; Unconventional Bonding In Organic Chemistry; Covalent Bonding In Transition Metal Clusters, Alan Wilfred Humason

Chemistry Theses and Dissertations

The geometries, chemical properties, and reactivities of molecules are determined by their electronic structure. The field of ab initio computational chemistry works to calculate the kinetic and potential energies between the nuclei and electrons of a molecule. These calculations usually begin with the determination the electronic ground state.

Molecules that cannot be adequately described with a single, ground state configuration are called \textit{multi-reference systems}, which require the calculation of a linear combination of all pertinent electronic configurations, with a corresponding increase in computational cost. This is not `black box' methodology, because solving these systems requires a good understanding of the …

Do Paraben Derivatives Alter T Cell Immunity?, Hailey Kintz

Spring Presentation of Undergraduate Research

T cells immunity is linked to a complex system of cytokines that determine differentiation of naïve T cells into Th1, Th2, Th17, and Treg cells. Estrogen production or periods of elevated production have been correlated with an anti-inflammatory state in which Th2 and Treg cells are up-regulated. Such responses in the immune system are capable of supporting pre-cancerous activity. We are investigating the tie between the xenoestrogen compounds found in cosmetics, parabens, and their ability to regulate T cell immunity. Testing parabens and paraben derivatives with weaker estrogen receptor association will allow for a better understanding of the interplay between …

Organocatalyzed Synthesis Of Epoxides From Chalcones Utilizing Amino Acids, Sabrina N. Kegeler

Masters Theses

The epoxide functional group is important throughout the chemical and pharmaceutical industries, as well as in nature. In the chemical industry, epoxides are present in resins and fragrances. In the pharmaceutical industry, epoxide-containing compounds are used as intermediates in the manufacturing of drugs. In nature, many natural products contain epoxide groups and are used for medicinal purposes, and for models to create synthetic molecules.

One approach to epoxide synthesis involves the use of an alkene precursor, a base, and an oxidizing agent. This is where my investigations began. The first step was to optimize the epoxidation reaction, examining substrate scope, …

Experiential Learning Activity: Biodiesel Inquiry Project, Ji Kim

Open Educational Resources

The activity described herein can be implemented in introductory chemistry and high school chemistry courses. The main goal of the project is to integrate a ubiquitous biodiesel production with experiential learning by providing a community-based project. The students work in groups, research the benefits of using biodiesel over petroleum-based diesel, collect waste cooking oil from home or restaurants, develop simple and cost-effective methods to produce biodiesel.

Surface Oxygenation Of Biochar Through Ozonization For Dramatically Enhancing Cation Exchange Capacity, Matthew D. Huff, Sarah Marshall, Haitham A. Saeed, James Weifu Lee

Chemistry & Biochemistry Faculty Publications

Background

Biochar cation exchange capacity (CEC) is a key property that is central to biochar environmental applications including the retention of soil nutrients in soil amendment and removal of certain pollutants in water-filtration applications.

Results

This study reports an innovative biochar-ozonization process that dramatically increases the CEC value of biochars by a factor of 2. The ozonized biochars also show great improvement on adsorption of methylene blue by as much as a factor of about 5. In this study, biochar samples treated with and without ozone were analyzed by means of pH and CEC assays, water field capacity measurement, elemental …

Serendipitous Discovery Of A New Method For The Catalytic Synthesis Of Indole-Fused Benzazepanes, Edward Gluzman, Paul A. Vadola

DePaul Discoveries

We report here on our investigations into the application of 1,5-hydride transfer cyclization mechanisms to the synthesis of 2,3-disubstituted benzofurans and indoles. We found that PtI₄ in MeCN at 120 ºC was indeed capable of activating the alkyne, however, the expected 2,3-disubstituted indole product was not observed. Instead we isolated an indolyl-3-benzazepane via an unexpected intramolecular Steven’s rearrangement/ring expansion. While this transformation has been previously reported our method may prove to have increased substrate scope and more practical reaction conditions. Further studies are underway to optimize the reaction conditions and to fully explore the scope and mechanism of the …

Substrate Specificity Of The Lipn Hydrolase From Mycobacterium Ulcerans, Stephanie Raynor

Undergraduate Honors Thesis Collection

Mycobacterium ulcerans is the causative agent of Buruli ulcer, a tropical skin disease that affects thousands of individuals annually. Recent studies have revealed that lipolytic enzymes are involved in the pathogenicity processes of mycobacterium and could be potential targets for novel antibiotics. LipN is one proposed serine hydrolase in Mycobacterium ulcerans that contains the conserved α/β hydrolase protein fold and utilizes the conserved catalytic traid of serine, histidine, and aspartate/glutamate. The physiological substrate and biological role of LipN from M. ulcerans have not yet been determined. In this study, LipN was cloned into a pET28a plasmid and overexpressed in an …

Solvent Free Vanadium Mediated Organic Transformations, Garrett Oberst

Undergraduate Honors Thesis Collection

A mixture of vanadium(V) oxide and copper sulfate was used to catalyze oxidative transformations in a variety of organic compounds. Multiple functionalities were tested, including thiols, amines and alcohols. Various transformations were observed resulting in various oxidized products, including coupling reactions. Reactions were performed in a solvent-free environment due to the insoluble nature of vanadium(V) oxide in common organic solvents. Results were analyzed using HNMR and GCMS.

Impact Of Ocean Acidification On Aphotic Biogeochemical Production Of Reactive Oxygen Species, Sarah Ann Murphy

Theses and Dissertations

Reactive oxygen species (ROS) are critical to global maintenance of the global organic carbon cycle, sulfur cycle, oxygen cycle, and transition metal cycles. The primary source of ROS is commonly considered to be photolysis or photochemically driven reactions, however ROS also exist in aphotic zones. A geochemical mechanism for the same in dark environments based on the tidally driven, episodic movement of anoxic groundwaters through oxidized, Fe(III) rich sediments is shown. Predictive models were developed based on in vitro experiments and tested using sediment samples collected from a saline tidal creek in the estuary at Murrell’s Inlet, South Carolina. These …

Facile Method For Large Scale Alignment Of One Dimensional Nanoparticles And Its Biomedical Application, Sheng Feng

Theses and Dissertations

Topographical cues can profoundly affect cellular behaviors. This thesis investigate how to utilize the topographical cues generated by two techniques, flow assembly and electrospinning, to regulate cellular behaviors.

First of all, a facile and robust method to align one-dimensional (1D) nanoparticles (NPs) in large scale has been developed. Using flow assembly, representative rod-like nanoparticles, including tobacco mosaic virus (TMV), gold nanorods and bacteriophage M13, have been aligned inside capillaries by controlling flow rate and substrate surface properties. The properties of 1D NPs, such as stiffness and aspect ratio, play a critical role in the alignment. Furthermore, these hierarchically organized structures …

Methodology Development In Green Chemistry: Oxoammonium Salt Oxidations And Fluoroform Incorporation, Rebecca J. Wiles

University Scholar Projects

Central to the advancement of small molecule synthesis is the ability to develop methodologies that reimagine well known chemistry in a new, environmentally friendly manner. In this thesis two central themes emerge: oxoammonium salt oxidations and trifluoromethyl incorporation using fluoroform gas. Several projects have been developed surrounding oxoammonium salt chemistry, which are featured by their mild conditions, ease of use, and the metal-free, recyclable nature of the oxidant. Trifluoromethylation using fluoroform gas finds its utility in the use of a potent greenhouse gas waste product as a benchtop reagent.

Methodology Development In Green Chemistry: Oxoammonium Salt Oxidations And Fluoroform Incorporation, Rebecca J. Wiles

Honors Scholar Theses

Central to the advancement of small molecule synthesis is the ability to develop methodologies that reimagine well known chemistry in a new, environmentally friendly manner. In this thesis two central themes emerge: oxoammonium salt oxidations and trifluoromethyl incorporation using fluoroform gas. Several projects have been developed surrounding oxoammonium salt chemistry, which are featured by their mild conditions, ease of use, and the metal-free, recyclable nature of the oxidant. Trifluoromethylation using fluoroform gas finds its utility in the use of a potent greenhouse gas waste product as a benchtop reagent.

Photogenerated O-Azaxylylenes: Mechanistic Studies And Synthetic Applications, William Cole Cronk

Electronic Theses and Dissertations

This research sets out to build upon excited state o-azaxylylene cycloaddition. The mechanism behind the excitation and cycloaddition process of photogenerated o-azaxylylenes was determined experimentally. Time-correlated single-photon counting, steady-state spectroscopy, triplet quenching experiments, and quantum yield studies provided evidence suggesting that excited state intramolecular proton transfer is followed by intersystem crossing and stepwise addition to the tethered unsaturated pendant.

In keeping with the principles of diversity oriented synthesis, a modular approach was taken to gain access to a diverse array of N,O,S-Polyheterocycles which were modified postphotochemically via Suzuki coupling to yield fused biaryls. Cycloaddition products, outfitted with halogens …

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 …

A Continuous Process Towards The Synthesis Of Quinolones, Stevara N. Clinton

Theses and Dissertations

Abstract

The development of quinolones is described from the first quinolone to the latest fluoroquinolones. Quinolones have generated considerable interest since their discovery because of their antibacterial capabilities. Analogs incorporating the 4-quinolone ring system comprise a largely expanding group of synthetic compounds. The development of antibacterial resistance has created the need for an efficient synthesis of quinolones that can be easily adapted toward the assembly of quinolone based antibacterial drugs.

There are several reported approaches to the 4-quinolone ring system. Many of these methods use expensive starting materials, require the removal of high boiling solvents, or use high temperature conditions …

Science Classics, Mark Masthay

Chemistry Faculty Publications

An essay on the impact of the works in the Imprints and Impressions: Milestones in Human Progress, an exhibition of rare books from the collection of Stuart Rose. Exhibition was held Sept. 29-Nov. 9, 2014, at the University of Dayton.

The Synthesis Of A Bisbenzothiophene (Bbt) Based Organic Semiconductor With Increased Function And Increased Solubility, Mary England

Senior Honors Theses

Organic semiconductors are growing in applications for use in modern technology.¹ The main interest in these molecules can be attributed to their low cost (compared to silicon) and their ability to be used on flexible substrates. There are four features that make a good organic semiconductor. First, the molecule should be conjugated, having alternating single and double bonds (lone electron pairs act similarly to double bonds). Secondly, the molecule should be planar, or flat, in shape. Thirdly, the molecule should have a narrow band gap to increase the overall conductivity. Lastly, the molecule should be soluble to ease application. …