Organic Chemistry Commons^™

The Emerging Applications Of Sulfur (Vi) Fluorides In Catalysis, Nicholas Ball, Cayo Lee, Jonathan E. Elisabeth, Nathan C. Friede, Glenn M. Sammis

Pomona Faculty Publications and Research

The past decade has witnessed remarkable growth of catalytic transformations in organic sulfur(VI) fluoride chemistry. This Perspective concentrates exclusively on foundational examples that utilize catalytic strategies to synthesize and react S(VI) fluorides. Key mechanistic studies that aim to provide insight toward future catalytic systems are emphasized.

The Regiochemistry And Relative Reaction Rates Of Methylbiphenyl Isomers In Electrophilic Aromatic Substitution Reaction (Eas) Nitrations Suggest A Non-Planar Geometry For 2-Methylbiphenyl While 3- And 4-Methylbiphenyl Remain Planar, Tristan Pj Wine

Honors Projects

Electrophilic aromatic substitution (EAS) reactions have long been a fundamental addition to sophomore-level organic chemistry classes, allowing students the opportunity to explore the electron donating and withdrawing effects of electrons contained in the substituents of the aromatic reactant. In this paper we present preliminary findings on the nitration of methylated biphenyls using kinetic and regioselective assessments to analyze steric influences on the planarization of 2-methylbiphenyl after EAS nitration. Our preliminary findings show that nitration favors the methylated phenyl ring of 2-methylbiphenyl, indicating that the steric influence of the methyl group restricts planarization of the carbocation intermediate. Furthermore, a competition nitration …

Elucidation Of Optoelectronic Properties Of Pyrrolo[3,2-B]Pyrrole Chromophores, Ryan Faddis

Symposium of Student Scholars

Ryan Faddis Abstract

Elucidation of Optoelectric Properties of Pyrrolo[3,2-b]pyrrole Chromophores

Ryan Faddis and Graham S. Collier

Department of Chemistry and Biochemistry

Kennesaw State University

Derivatives of phenyl substituted pyrrolo[3,2-b]pyrroles have shown promise of being useful organic opto-electric compounds due to their advantageous tunability through careful synthetic design. Furthermore, one pot synthesis and readily accessible commercial reactants such as, aromatic amines and aldehydes, makes these molecules more favorable than other, more complex syntheses traditionally required for optically active organic molecules. Although relatively simple synthesize, more information from experimentation is needed to understand the optical properties of these species, and thus, a …

The Reactivity Of Metal Phosphites: Oxidative Rate Analysis, Jamie Kitchens

Symposium of Student Scholars

Phosphorous compounds are involved in many of the biomolecular processes deemed fundamental for life. DNA, ATP, and phospholipids are a few of the molecules where phosphates can be found in the body. Phosphates are geochemically characterized by their low solubility and poor reactivity. This has led to the investigation of reaction mechanisms that could lead to the formation of the phosphorous compounds found in organisms. The oxidation of phosphite into phosphate could be how phosphates were introduced to life, due to phosphites being more soluble and more reactive than phosphates. We will present the synthesis and oxidation reactivity of four …

The Chemistry Of Fermentation As It Relates To The Art Of Winemaking, Olivia Cochran

Symposium of Student Scholars

The process of fermentation can be traced back to the beginning of civilization. Countries, over time, have learned this scientific process and turned it into the backbone of their culture through the making and manufacturing of wine. While climate-change and global-warming have impacted the commercial marketability of wine, the scientific process has remained constant. This undergraduate project analyses the production, fermentation and analytical approach of producing high quality wine. Beginning from the picking of grapes, to testing the acidity through a series of titrations, winemaking is truly where science and art collide.

Advancing The Preclinical Development Of Secondary Metabolites From Cacospongia Mycofijiensis For The Treatment Of Cancer, Joseph Morris

Natural Sciences and Mathematics | Biological Sciences Master's Theses

The marine sponge Cacospongia mycofijiensis from the Indo-Pacific has proven to be a source of structurally diverse secondary metabolites that are biologically active against a variety of distinct targets. Current interest in the secondary metabolites of C. mycofijiensis largely stems from a) their potent and preferential cytotoxicity for cancer cell lines versus normal cells, making many of them promising leads as cancer therapeutics and b) the novel mechanisms of action responsible for their impressive cytotoxicity. However, limited compound availability has resulted in a paucity of studies aimed at advancing the preclinical development of these secondary metabolites from C. mycofijiensis for …

Methodology Utilizing Triphosgene To Promote Cyclization Of Epoxy Ketones To Pyranoside Derivatives Via Proposed Epoxonium Ions, Isaac Camargo Dos Reis

LSU Master's Theses

The development of new methodologies in organic chemistry is of great importance. In fact, the discovery and creation of new reactions frequently uncovers new chemical reactivities and creates new areas of chemistry. The purpose of this thesis is to present the development of new synthetic reactions that were discovered through previous findings. Additionally, the main theme of this work relies on the intermediacy of a cationic reactive intermediate: epoxonium ions. Chapter 1 provides a brief review of bicyclic epoxonium ions and methods for their generation, as well as their utility in the synthesis of interesting heterocycles. Furthermore, Chapter 1 illustrates …

Records Of Enriched Uranium Atmospheric Deposition In Pond Sediments In Piketon, Oh, Brianna Herner, Brian Majestic, Michael Ketterer

DU Undergraduate Research Journal Archive

The enrichment of uranium, often for nuclear weapons programs and commercial nuclear reactors, produces higher concentrations of radioactive uranium 235 (²³⁵U) than what naturally occurs, which can pose a human health hazard. The most abundant naturally occurring uranium isotope is ²³⁸U, which is still radioactive, however a higher concentration of ²³⁵U skews the observed isotopic uranium distribution. The Department of Energy Portsmouth Gaseous Diffusion Plant, located near Piketon, OH, enriched uranium from 1954 to 2001 and ²³⁵U pollution has recently been detected in air and sediment samples in the surrounding community. The extent of the …

Cu-Promoted C-H Bond Hydroxylation Inspired By Cu-Dependent Metalloenzymes, Rachel Trammell

Chemistry Theses and Dissertations

From 2003 to 2015, Schӧnecker and Baran proposed a dinuclear Cu/O₂ species in their mechanistic proposal for the hydroxylation of sp³ C-H bonds within their systems (proposed based on yields). Inspired from the site selectivity of this methodology and poor analysis of the mechanism, the first project was inspired to re-examine the sp³ C-H bond hydroxylation by Schrӧnecker and Baran and perform an intensive investigation into understanding how Cu/O₂ interact which led us to propose a new mechanism based on the evidence collected (i.e., LCu^II-hydroperoxide species that undergoes homolytic O-O bond cleavage). From there …

Reeling In New Antibiotics: Synthesis And Antimicrobial Susceptibility Testing Of Zinc-Binding Clavanins From Styela Clava (Sea Squirt), Eduardo Badillo-Colberg

Honors Scholar Theses

Clavanins have been a quite rarely studied antimicrobial peptide (AMP) family. Though the data in the few studies published on the matter and in theoretical experimental data presented by the Wang lab in their peptide library creation [14], in that the members of this family could potentially be quite effective novel antimicrobial candidates. Among those that have been targets of studies, Clavanin A has been at the forefront of this endeavor of finding effective novel antimicrobial peptides[14]. In these aforementioned studies, Clavanin A has been shown to be quite effective against many different bacterial strains, which begs the question as …

One-Pot Synthesis Of Disubstituted Primary Amines From Nitriles Via Grignard Addition And Metal-Alcohol Reduction, Joshua Peltan

Honors Theses

The process of developing a working base case procedure for a novel one-pot-two-step synthesis of primary amines from Grignard reagents, nitriles, sodium metal or alkali metal loaded silica gel, and alcohol is described. Initial steps towards applying the process broadly are detailed. The process has the potential to be an affordable, convenient, safer, greener, and more accessible alternative to exiting methods of accomplishing the same transformation. The reaction scheme has been proven to provide yields and purity comparable to existing methods for certain pairs of substrates; however, its utility as a general-purpose method for transforming arbitrary pairs of Grignard reagent …

Investigations Into Effects Of Modified Prolines On Cis-Trans Isomers And Polypeptide Secondary Structure & Prediction Of Spectroscopic Properties Of Phthalonitriles For Characterization, Jeffrey Raab

Seton Hall University Dissertations and Theses (ETDs)

Proline is a unique amino acid because it is the only amino acid whose side chain wraps around and bonds back to the peptide backbone. This ring shape helps proteins form conformations which would otherwise not be possible such as hairpin turns. The cis/trans isomerization of the peptide bond between the preceding amino acid (X_aa) and Proline is important in determining how the secondary structure folds. Thus, being able to control the cis/trans isomerization is important when a specific conformation is desired; Proline can be modified to get make the equilibrium shift whichever way is needed. The modifications …

Game-Based Learning In Science: Can Video Games Simplify Organic Chemistry?, Rachel Israel

Senior Honors Theses

Organic chemistry has been taught in the same way for decades, and students still have difficulty understanding and comprehending the subject material. Perhaps it is time to change the methods by which this subject is taught. Video games have been successfully used in education to create learning environments that increase student motivation and engagement as well as challenge students and promote collaboration. It is difficult for students to maintain a growth mindset in organic chemistry within the classroom. However across different genres, video games create a unique environment where an individual is encouraged to try again when they fail. This …

Effects Of Halogen Bonding On 13c Nmr Shifts Of Various Tolan Species, Anthony Lybrand

Honors Theses

Halogen bonding is slowly becoming a more and more useful part of the world of chemistry and is beginning to be incorporated into various aspects of the chemical industry. This study’s purpose is to determine whether or not halogen bonding can cause any effect in the 13C NMR shifts. The specific purpose of this study is to determine whether these chemical shifts change when a Lewis Base is added to the dissolved sample. In order to do this, the tolan species (4-iodotolan and 4-chlorotolan) had to be synthesized. Once synthesized, the tolan species were analyzed via NMR. NMR data indicated …

Applications Of Sodium Azide In The Synthesis Of Tetrazines And Hydrolysis Reactions, My Le

Honors Theses

The inverse electron demand Diels−Alder cycloadditions of heterocyclic azadienes have provided a robust methodology for synthesizing highly substituted and functionalized heterocycles. It is widely used in organic synthesis and the pharmaceutical industry in the divergent construction of screening libraries and bioorthogonal conjugation. Each heterocyclic azadiene was found to possess a unique reactivity toward different classes of dienophiles, display predictable modes of cycloaddition, and exhibit substantial substituent electronic effects impacting their intrinsic reactivity and cycloaddition regioselectivity. Synthesis of 1,2,4,5-tetrazine has been reported in the literature since the late 19th century, showing scientists' tremendous interest in its application.

Herein we attempt to …

End Group Modification Of Linear Dendritic Block Copolymers (Ldbcs), Chinwe Udemgba

Honors Theses

Linear dendritic block copolymers are amphiphilic molecules that consist of a dendritic hydrophilic portion and a linear hydrophobic portion. Its unique ability to self-assemble into spherical nanoaggregates while having the potential to uptake and transport both hydrophilic and hydrophobic drugs makes these polymers an item of interest in regard to the drug delivery field. The synthesis of polyamidoamine-polylactide linear dendritic block copolymers was designed to address the common issues in drug delivery systems, including problems in permeability, solubility, stability, specificity, and retention. Though this linear dendritic block copolymer has previously been synthesized in our lab with cationic amine surface functionalities, …

The Power Of Sulfur: A Study Of An Isothiocyanate Chiral Derivatizing Agent, Thioamide Based Chiral Solvating Agents, And The Geometry Of Sulfonamides, Emily B. Crull

Dissertations

This three-part dissertation is connected by the thread of utilizing sulfur-based functional groups, hence the power of sulfur. The first project was the development of a pentafluorobenzene based isothiocyanate chiral derivatizing agent (CDA), a class of compounds that differentiate enantiomers through covalent bond formation. This project, which was addressed using a combination of synthetic and computational methods and NMR analysis, gave rise to an CDA that was highly selective for amines and computationally predictable. Branching off of that, the second project demonstrated the use of two thioamide chiral solvating agents (CSAs), which had never been reported as a core functional …

Organic Synthesis For Solving Clinical Conundrums Of Drug Activation And For Facilitating Natural Product Drug Discovery, Elkin Libardo Romero

Open Access Theses & Dissertations

Organic chemistry is an exploratory world in which chemists translate their knowledge by creating new molecules and explore their biological and physical properties. For the past three years, our research has been focused on organic synThesis and chemical biology to solve challenges in this area. Two major approaches have been faced: First, the chemical synThesis of the active metabolite of antithrombotic prodrug Plavix (clopidogrel). Clopidogrel (CPG) has been widely used as an antithrombotic prodrug, which undergoes extensive metabolism in patients; among it, only a trivial portion is converted through a series of cytochrome P450 (CYP)-catalyzed thiophene degradation to form active …

Analyzing The Lysergic Acid Amide Content Extracted From The Seeds Of Argyreia Nervosa Via The Use Of Lc-Ms, Elisabeth Barone

Forensic Science Master's Projects

Psychedelic plant use by humans can be traced back centuries to the times when early cultures used these plants in activities ranging from healing rituals to religious ceremonies. In recent years, several of these plants have reemerged on the drug scene and are currently being marketed as “legal highs” (since the plant seeds are legal to purchase through a variety of online vendors). With the growing number of internet forums where recreational drug users can write about their experiences and share them with others, it has become relatively simple for almost anyone to obtain the materials necessary to experience a …

Theranostic Nanoparticles Folic Acid-Carbon Dots-Drug(S) For Cancer, Godwin Kweku Babanyinah

Electronic Theses and Dissertations

This study aims to prepare theranostic nanoparticles (NPs) that are expected to increase cancer diagnostics and therapeutic efficacy. We prepared the NPs constituting carbon dots (CDs) as an imaging agent, folic acid as a targeting agent, doxorubicin (DOX), or gemcitabine (GEM) as chemotherapy agents. The NPs include noncovalent FA-CDs-DOX, covalent CDs-FA-DOX, and covalent FA-CDs-GEM. Through ultraviolet-visible spectroscopy, fluorescence spectroscopy, and Fourier transform-infrared spectroscopy, the fabrication of these NPs was confirmed. It was discovered that the high drug loading efficiency is the noncovalent series while the high drug loading capacity is the covalent series The in-vitro pH-dependent drug release data indicate …