Organic Chemistry Commons^™

Student-Faculty Research In Organic Chemistry, Timo V. Ovaska

Honors and Awards Speeches and Programs

Timo Ovaska remarks that the clothes we wear, the colors we see, the foods we eat, the fuels that power our cars, the medicines that make us heal and feel better, even the biochemical reactions that happen in our bodies are all manifestations of the importance of organic chemistry in daily life.

He also praises his students who chose to do research, as there is no mandatory research component for the chemistry major at Connecticut College, who have gone on to successful careers. Students chose to get involved not because it was going to be easy, but because they were …

Energy Densification Via Hydrothermal Carbonization, Keri Noack

Festival of Communities: UG Symposium (Posters)

A process called hydrothermal carbonization (HTC), also known as wet torrefaction involves treatment of raw biomass in hot, pressurized water. HTC of woody biomass has been shown to significantly increase the energy density of the feedstock, producing a biochar, similar to coal, having up to 40% higher calorific energy content. Feedstocks investigated include Tahoe chips, Pinion/Juniper chips, Rice hulls, and Corn Stover pellets pre-treated at 215 °C, 255 °C, and 295 °C. Chemical analyses were conducted on the gaseous, aqueous, and solid HTC products. Energy contents of the solid biochar products were measured by calorimetry, and mass balances were determined.

Predicting Homo And Lumo Energy Gaps For Organic Semi-Conductor: A Theoretical Study, Padtaya Pukpayat

Festival of Communities: UG Symposium (Posters)

This poster presents a theoretical approach for characterizing the electronic properties of novel electron-deficient organic semiconductors containing variety of electron donor substituents. In treating these compounds, the following questions will be addressed: What effects to the bandgap will each substituent have? Will any of the substituents lower the band gap to the desired range for solar cell applications(<2.0eV)? Can we use the current, inexpensive and tractable computational methods as a predictive tool for guiding future experimental design of organic based solar cells, rather than depending solely on experimental procedures?

Trypanosoma Cruzi - Derived Sugar Epitopes - Synthesis And Immunology, Erika Y. Monroy^, Roger A. Ashmus, Jamal Khamsi, Andrew Pardo, Nathaniel S. Schocker, Rosa A. Maldonado, Kayla Vasquez, Alexandre F. Marques, Igor C. Almeida, Katja Michael*

COURI Symposium Abstracts, Spring 2011

The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease. As of today no effective vaccine has been developed for it. Certain developmental stages of T.cruzi express cell surface oligosaccharides with terminal alpha-galactosyl and rhamnosyl residues, which are believed to be highly immunogenic in humans. The exact structures and sizes of these epitopes are still unknown. Our quest is to shine light on the chemical structures of immunogenic alpha-Gal and alpha-Rha containing mono-, di-, and trisaccharides that are conjugated to a keyhole limpet hemocyanin (KLH) carrier protein through a combination of chemical synthesis and immunological studies. The compounds …

Spectroscopic (Ir, Nmr, Uv-Vis), Theoretical Study And Optical Properties Of 9,10-Dihydrobenzo(A)Pyrene-7(8h)-One And 7, 8, 9, 10-Tetrahydrobenzo(A)Pyrene, Mireya Martinez

Undergraduate Research Conference

Polycyclic aromatic hydrocarbons (PAHs) are organic molecules found in the environment. The PAHs are formed from incomplete combustion, are found in diesel exhaust particles, grilled foods, gas burners, emission from wood, and cigarette smoke. These compounds are known to be carcinogenic and mutagenic1,2. Spectroscopic studies were performed on two PAHs, 9,10- dihydrobenzo(a) pyrene-7(8H)-one and 7,8,9,10- tetrahydrobenzo(a)pyrene, which helped to characterize them. Also, a theoretical infrared study was done on 9,10-H2BaP, a scaling factor was found for a simulated infrared spectrum.

A Sodium Salt Of The Dimer Of Boronoterephthalic Acid Anhydride, Scott Simmons, Albert Fratini, Vladimir Benin

Chemistry Faculty Publications

The title compound, sodium bis­(6-carb­oxy-1-hy­droxy-3-oxo-1,3-dihydro-2,1-benzoxaborol-1-yl)oxidanium, Na+·C16H15B2O13-, was prepared in two steps from 2-bromo-p-xylene. Its crystal structure was determined at 140 K and has triclinic (P) symmetry. The compound presents a unique structural motif, including two units of the cyclic anhydride of boronoterephthalic acid, joined by a protonated, and thereby trivalent, oxonium center. Association in the crystal is realized by complementary hydrogen bonding of the carboxyl groups, as well as by coordination of the sodium cations to the oxygen centers on the five-membered rings.

Theoretical Investigation Of A Reported Antibiotic From The 'Miracle Tree' Moringa Oleifera, Michael Horwath, Vladimir Benin

Chemistry Faculty Publications

Moringa oleifera, sometimes called the “Miracle Tree,” has received international attention for its potential to improve health in impoverished tropical areas. In addition to high vitamin content in the leaves and pods, the tree contains compounds with antioxidant and antibacterial properties. This study focused on the theoretical investigation of the suggested structure of one antibacterial compound, “pterygospermin,” whose existence was proposed after some studies of the roots of M. oleifera. The structure of pterygospermin was first proposed by a research group working in the 1950s, but later studies have not found evidence of this compound and have instead …

Synthesis Of Pyridine-Based Ligands As Potential Magnetic Liquid Crystals, Jacqueline Gamboa Varela^, Jose E. Nunez*

COURI Symposium Abstracts, Spring 2011

Ligands for the development of metallomesogens (metal-containing-liquid-crystals) have attracted attention due to potential applications in materials science such as optical devices, magnetic switches, and conductors. The attempts to synthesize bis(3-alkoxy) pyridine amines are presented. These structures are designed to exhibit liquid crystalline properties as metal complexes. Reaction conditions using potassium carbonate and potassium tert-butoxide as bases under Ullmann-type conditions in various solvents (aromatic and non-aromatic), between -78 ⁰C to 160 ⁰C, have been unsuccessful. It is imperative to understand the electronic effects of the meta-substituted pyridine precursors to further develop the copper-catalyzed conditions of these types of molecules.

Bis( N, N-Dipheny-3-Pyridineamine) Tungsten Complex As Molecular Gyroscope, Verenice Ramirez^, Jose E. Nunez*

COURI Symposium Abstracts, Spring 2011

In recent years, the interest in molecular machines has increased based on inspiration from macroscopic machines, such as gyroscopes applied in racecar engines and arrays of gyroscopes in automatic pilot functions. The same concept has been taken down to the nanoscopic level as molecular machines in solution like bevel gears and turnstiles, but for application use they must be in the solid state. Gyroscope molecules can exhibit fast rotation and the aim is to design free rotation in the crystal lattice that maintains volume conserving motion. Bis(N,N-diphenyl-3-pyridinamine) tungsten complex was prepared by irradiation of tungsten hexacarbonyl in the presence of …

Polymorphs And Hydrates Of Acyclovir, Katie M. Lutker, Rosalynn Quiñones-Fernández, Jiadi Xu, Ayyalusamy Ramamoorthy, Adam J. Matzger

Chemistry Faculty Research

Acyclovir (ACV) has been commonly used as an antiviral for decades. Although the crystal structure of the commercial form, a 3:2 ACV/water solvate, has been known since 1980s, investigation into the structure of anhydrous ACV has been limited. Here, we report the characterization of four anhydrous forms of ACV and a new hydrate in addition to the known hydrate. Two of the anhydrous forms appear as small needles and are stable to air exposure, whereas the third form is morphologically similar but quickly absorbs water from the atmosphere and converts back to the commercial form. The high-temperature modification is achieved …

Synthesis Of Hydroxy- And Polyhydroxy-Substituted 1,3-Diaminocyclohexanes, Anobick Sar, Sergey V. Lindeman, William A. Donaldson

Chemistry Faculty Research and Publications

The synthesis of hydroxy-trans-1,3-diaminocyclo­hexanes based on nitroso-Diels-Alder cycloaddition of (cyclohexadienyl)phthalimide is reported.

Gram Scale Synthesis Of The C(18)-C(34) Fragment Of Amphidinolide C., Nicholas A Morra, Brian L Pagenkopf

Chemistry Publications

The synthesis of the C(18)-C(34) fragment of amphidinolide C has been achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment. The highly convergent approach will facilitate the synthesis of analogues, including the C(18)-C(29) fragment of amphidinolide F. Synthetic highlights include the selective methylation of a diyne, and the highly efficient use of a second generation cobalt catalyst in the Mukaiyama oxidative cyclization to form the trans-THF ring.

Utilization Of Dna/Dendron Conjugates For Dna Monolayers On Gold: A Comparative Study, Erik Steven Vint

Theses, Dissertations and Capstones

The uses of single-stranded DNA probes tethered to solid supports have gained interest in recent years due to the increasing number of applications these systems present. However, the traditional methods used to fabricate these monolayers are flawed. The synthesis and purification of multithiol headgroups for improvement upon ssDNA surface attachment for the fabrication of self-assembled monolayers on gold surfaces is described. Generation 4 polyamidoamine dendrons were conjugated to ssDNA oligomers in a one-to-one ratio and functionalized to provide multiple thiol groups for possible surface attachment. Modification of the dendrimer’s amine terminated periphery groups to thiols was confirmed using 1 H …

Enantiocontrolled Solid-State Photodimerizations Via A Chiral Sulfonamidecinnamic Acid, Kraig A. Wheeler, Joshua D. Wiseman, Rebecca C. Grive

Faculty Research and Creative Activity

The supramolecular patterns of three polymorphs of a chiral sulfonamidecinnamic acid reveal components effectively organized into predetermined hydrogen-bonded dimers with favorable <3.8A ° olefin spacing for enantioselective single-crystal-to-single-crystal [2 + 2] photodimerization reactions.

Synthesis Of N-Acetyl And C-Tert-Butyl Natural Amino Acid Substrates That Mimic Residues Of Polypeptides And Their Reactivity With [Feiv(O)(N4py)]2+: Kinetic And Mechanistic Investigations, Ashley Ann Campanali

Wayne State University Dissertations

This dissertation is divided into two chapters, the first chapter includes an introduction to reactive oxygen species and their reactions with proteins. The introduction also covers metal-based oxidants, including both heme and non-heme enzymes that activate dioxygen as well as complexes that mimic these enzymes. The work discussed in chapter one concerns the synthesis of amino acid substrates that mimic amino acid residues. Substrates synthesized were derived from Gln, Asn, Ile, Cys and Tyr. Once synthesized, these substrates were reacted with [FeIV(O)(N4Py)]2+ under pseudo-first order conditions. The mechanisms for the reactions of the most reactive substrates were investigated. Electron-transfer proton-transfer …

Development Of Chemical Inducers Of Dimerization For Screening Competitive Histone Deactelyase Inhibitors, Emily Lynn Aubie

Wayne State University Dissertations

Histone Deacetylase (HDAC) proteins are transcriptional regulators that affect histone proteins, which are involved in packaging of DNA into chromosomes. HDACs have been linked to the proliferation of cancer through their role in transcriptional regulation. Due to these findings, HDAC inhibitors have been explored as anti-cancer agents. Several HDAC inhibitors are currently in various stages of clinical trials, and the inhibitor suberoyl anilide hydroxamic acid (SAHA) has been FDA approved for treatment of cutaneous T-Cell lymphoma. Currently, most of the known HDAC inhibitors are non-selective, which causes non-specific binding to the active sites of all HDAC isoforms, including those not …

Chemical Synthesis Of Peptides And Peptide Thioesters, Indrajeet Sharma

Wayne State University Dissertations

This dissertation describes investigations toward the development of a new chemistry for the block synthesis of peptides and peptidyl thioesters. A direct approach for the Fmoc-SPPS of peptidyl thioesters is also delineated in this thesis.

In the first part of chapter one, the difficulty and importance of chemical synthesis of peptides is explained, and a brief survey of available methods is given. The second part of chapter one presents the challenges inherent in the synthesis of peptidyl thioesters by Fmoc-SPPS.

The second chapter outlines the investigations conducted towards the development of a new chemistry for epimerization-free block synthesis of peptides …

Synthesis Of Peptide-Ligand Conjugates And Their Applications, Nitinkumar Dilipkumar Jabre

Wayne State University Dissertations

Three research areas pertaining to this dissertation, (i) synthesis strategies of peptide-ligand conjugates, (ii) their applications and (iii) chemistry of ferryls were surveyed in the introduction chapter. Next, the divergent and dual divergent strategies for the synthesis of non-heme ligand-peptide conjugates were developed. Using these strategies various peptide-ligand conjugates were synthesized via solution as well as solid phase synthesis. The scope and the functional group compatibility of these strategies were also established. The utility of the dual divergent strategy has been demonstrated by synthesizing a small library of metal-binding LHRH analogues. This work showcased the ability of the dual divergent …

Fourier Transform Mass Spectrometry For The Molecular Level Characterization Of Natural Organic Matter: Instrument Capabilities, Applications, And Limitations, Rachel L. Sleighter, Patrick G. Hatcher, Goran Nikolić (Ed.)

Chemistry & Biochemistry Faculty Publications

No abstract provided.

Synthesis And Characterization Of Diallylic Polysulfanes And Study Toward The Synthesis Of Thiarubrine E, Kai Wang

Legacy Theses & Dissertations (2009 - 2024)

Garlic oil contains diallyl polysulfanes as major components, which have been used as environmentally benign bird repellants and nematicides. While previous studies found that the biological activity of polysulfanes increases with numbers of sulfur atoms, higher diallyl polysulfanes are currently unavailable. A simple approach was developed, using liquid sulfur as a reagent, to the synthesis of diallyl polysulfanes containing chains of more than 20 sulfur atoms. This method was successfully applied to other diallylic disulfides and to garlic oil to give new families of polysulfanes. Some diallyl polysulfanes were isolated in a pure form by preparative high performance liquid chromatography …

Design And Synthesis Of Novel Agrofungicides Based On Naturally Occurring Pbdes, Robert Alexander Smith

Electronic Theses and Dissertations

Cyanobacterial symbionts of Indo Pacific marine sponges, e.g. Dysidea sp., produce hydroxylated (OH-) polybrominated diphenyl ethers (PDBEs) which likely function as chemical deterrents owing to their antifungal and antibacterial properties. Limiting the therapeutic potential and agricultural use of these antimicrobial natural products are the negative connotations associated with non hydroxylated anthropogenic PBDEs. Anthropogenic PBDEs are pervasive global pollutants used as flame retardant additives in many household goods, e.g. furniture, textiles, and electronics. These molecules have a propensity to bioaccumulate in living organisms, they easily traverse the trophic food chains, they are readily passed from mother to offspring, and many of …

I, An Improved Procedure For Alkene Ozonolysis. Ii, Exploring A New Structural Paradigm For Peroxide Antimalarials., Charles Edward Schiaffo

Department of Chemistry: Dissertations, Theses, and Student Research

The use of ozone for the transformation of alkenes to carbonyls has been well established. The reaction of ozone with alkenes in this fashion generates either a 1,2,4-trioxolane (ozonide) or a hydroperoxyacetal, either of which must undergo a separate reduction step to provide the desired carbonyl compound. There is considerable interest in being able to perform a reductive ozonolysis to directly provide the carbonyl. Previous reports from the Dussault lab have shown that amine N-oxides are able to perform a reductive ozonolysis. In the course of efforts to expand this reaction to other oxyanions it was realized that water was …

Synthesis, Characterization, And Properties Of Homometallic Dinuclear Ruthenium Complex Containing Chloro-Phenanthroline And Bipyridine, A. A. Bhuiyan, S. Kudo

Journal of the Arkansas Academy of Science

This paper deals with the synthesis and spectroscopic investigation of homometallic dinuclear ruthenium(II) complex containing chlorophenanthroline and bipyridine ligands. This bimetallic ruthenium polypyridine complex may be useful for biological electron transfer studies. Heteroleptic ruthenium monomer complex Ru(bpy)2(Cl-phen) (where bpy = 2,2’-bipyridine and Cl-phen = 5-chloro- 1,10-phenanthroline) was prepared in a two step procedure previously developed in our laboratory. This monomer complex was used to prepare the ruthenium dimer complex, (bpy)2Ru(phen-phen)Ru(bpy)2, by utilizing the Ni-catalyzed coupling reaction. Both the complexes were purified by column chromatography. The identity and the integrity of the complexes were confirmed by elemental analysis as well as …

Partially Halogenated Acenes And Heteroacenes For Organic Electronics, Balaji Purushothaman

University of Kentucky Doctoral Dissertations

Inorganic materials have dominated electronic applications such as photovoltaic cells, thin film transistors (TFTs) and light emitting diodes (LEDs). However developments in the field of organic electronics over the past three decades have enabled the use of organic materials in these devices. While significant improvements have been made to improve their electronic properties there are several road blocks towards commercial application. One of the significant obstacles is the poor charge carrier mobility associated with organic semiconductors processed by well established printing methods. The goal of my research project is to improve the charge carrier mobility of solution cast films of …

Specific Incorporation Of Unlabeled Aromatic Amino Acids Into 15n-Labeled Sac7d Through Use Of Glyphosate, Paul Ferguson, Mary Catherine Hames

Summer Community of Scholars Posters (RCEU and HCR Combined Programs)

No abstract provided.

Synthesis Of Small Molecule Inhibitors Of Janus Kinase 2, Phosphodiesterase Iv, Gabaa And Nmda Receptors: Investigation Of Mcmurry, Mannich And Chemoenzymatic Strategies, Meghanath Gali

USF Tampa Graduate Theses and Dissertations

Stilbenoids possess a wide range of biological properties such as, anticancer, antiplatelet aggregation, antiestrogenic, antibacterial, antifungal and antiatherogenic, etc. Owing to these therapeutic values, a great deal of attention attracted in the synthesis of derivatives of stilbenes. During the course of the study, G6 a novel stilbenoid was discovered, through high throughput screening, to be a potent inhibitor of mutated JAK2-V617F. The mutated JAK2 variant has been implicated in various myeloproliferative disorders (MPDs) including polycythemia vera (PV), essential thrombocythemia (ET) and primary myelofibrosis (PMF) has been targeted by therapeutics. Chapter 2 describes the synthesis of analogs of the stilbenoid G6 …

Chemical Investigation Of The Antarctic Marine Invertebrates Austrodoris Kerguelenensis & Dendrilla Membranosa And The Antarctic Red Alga Gigartina Skottsbergii, John Alan Maschek

USF Tampa Graduate Theses and Dissertations

The marine realm and, in particular, the Antarctic benthos is largely unexplored and understudied. The chemical investigation reported herein reveals not only the biodiversity, but how that biodiversity manifests remarkable chemical diversity. In our continuing study of the nudibranch Austrodoris kerguelenensis, we have isolated a diverse suite of diterpenoid glyceride esters, palmadorins D - S (2.32 - 2.47), one of which is the first reported halogenated diterpene from a dorid nudibranch. Utilizing genomic data from collaborators, we have investigated the chemical diversity from phylogenetically unique specimens collected in close proximity to one another. Chemical groupings based on comparison of LC/MS …

Lead Discovery And Optimization Strategies Towards The Development Of 4(1h)-Quinolones And 1,2,3,4-Tetrahydroacridone Analogs With Antimalarial Activity, Richard Matthew Cross

USF Tampa Graduate Theses and Dissertations

The goal of our research endeavor was to successfully employ modern lead discovery and optimization strategies towards the development and identification of compounds possessing antimalarial activity. Preliminary data from in vitro screening at the Walter Reed Army Institute of Research identified several chemotypes including 4(1H)-quinolones and 1,2,3,4-tetrahydroacridones to have potent antimalarial activities. Multiple synthetic routes were devised and implemented which enabled the rapid preparation and isolation of over 400 structurally diverse 4(1H)-quinolones and 1,2,3,4-tetrahydroacridones.

Our research towards discovering and optimizing antimalarials was inspired from the severe impact malaria has had on our planet especially on impoverished countries. There are over …

Synthesis And Antimicrobial Activities Of S,S'-Heterosubstituted Disulfides, Praveen Ramaraju

USF Tampa Graduate Theses and Dissertations

Antibiotic resistance is a particularly critical health concern and has increased dramatically over the past two decades. For over a decade the Turos laboratory has been designing small molecules to target pathogenic microbes such as Staphylococcus aureus and the resistant variants like methicillin-resistant Staphylococcus aureus (MRSA). Previously, N-thiolated Β-lactams, N-thiolated 2-oxazolidinones and aromatic disulfides that were synthesized in Dr. Turos' lab have shown strong activity against these bacteria. The present work describes the synthesis and antimicrobial activities of a related structural class called S,S'-heterosubstituted disulfides. For ages, sulfur (elemental) has been used as an antibacterial for controlling infestation and bacterial …

Effect Of A Strategically Positioned Methoxy Substituent On The Photochemistry Of 3-Aryl-3h-1-Oxacyclopenta[L]Phenanthren-2-Ones, Roshini Thumpakara, Binoy Jose, Perupparampil Unnikrishnan, Sreedharan Prathapan, Nigam Rath

Chemistry & Biochemistry Faculty Works

Irradiation of 3-methoxy-3-aryl-3H-1-oxacyclopenta[l]phenanthren-2-one derivatives 5a–d resulted in singlet-mediated decarbonylation reaction leading to the formation of phenanthrene derivatives 9a–d. The structure of the photoproduct was unequivocally established on the basis of X-ray crystallographic analysis.