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Articles 1 - 30 of 31
Full-Text Articles in Organic Chemistry
Investigation Of The Analytical Utility Of The Inductively Coupled Plasma Mass Spectrometer (Icp-Ms) For The Quantification Of Proteins Via Lanthanide Labeling, Caitlin Elizabeth Dunlap
Investigation Of The Analytical Utility Of The Inductively Coupled Plasma Mass Spectrometer (Icp-Ms) For The Quantification Of Proteins Via Lanthanide Labeling, Caitlin Elizabeth Dunlap
Undergraduate Honors Thesis Collection
The discovery and ability to provide an absolute concentration of biomarkers in the body can facilitate early diagnoses of diseases. This information can also be used for more accurate and unique treatments for those patients. While major advances in molecular mass spectrometry allows for a sensitive identification of these biomarkers, they are limited to only four orders of magnitude in their dynamic ranges. Due to this, detection and quantitation of low abundant proteins, which tend to make up these vital biomarkers, is very difficult. On the other hand, ICP-MS offers a wider dynamic range (up to 12 orders of magnitude) …
Nucleic Acid Editing By Adenosine Deaminase Enzymes, Josey Rae Mckinley
Nucleic Acid Editing By Adenosine Deaminase Enzymes, Josey Rae Mckinley
Undergraduate Honors Thesis Collection
RNA editing is crucial to the genetic diversity and structural complexity of organisms. ADAR (adenosine deaminase acting on RNA) is an RNA editing enzyme that creates a mutation of adenosine to inosine. The human ADAR2 (hADAR2) enzyme is known to edit RNA; however, it contains minor sequence homology with the cytidine deaminase enzymes, APOBEC and AID, which are known to edit both DNA and RNA (11 & 12). The ability of hADAR2 to edit DNA was tested through transformation into the Saccharomyces cerevisiae yeast strain BY4741. DNA editing was tested by determining if the transformed yeast became resistant to the …
Producing Dihydrofurans Using Palladium (Ii) Catalyst And Optimized Base, Chandler Mitchell
Producing Dihydrofurans Using Palladium (Ii) Catalyst And Optimized Base, Chandler Mitchell
Undergraduate Honors Thesis Collection
Dihydrofurans serve as building blocks for other compounds in organic synthesis. The main goal of this project was to discover an efficient and relatively inexpensive pathway for producing monosubstituted dihydrofurans in high yield from cyclic boronic half acids. Aldehydes were converted to homoallylic alcohols by the addition of allylmagnesium bromide. The alcohols were then transformed into cyclic boronic half acids using ringclosing metathesis with Grubbs 1st Generation Catalyst and alkenyl boronic esters. Finally, monosubstituted dihydrofurans were produced using a palladium (II) catalyst with a base. Palladium (II) catalysts that were tested include [1,1'- bis(diphenylphosphino)ferrocene]palladium (II) dichloride, palladium (II) acetate with …
Quantitative Analysis Of Acetic Acid In Hard Woods As A Way To Improve Museum Artifact Storage, Alexandria Flora
Quantitative Analysis Of Acetic Acid In Hard Woods As A Way To Improve Museum Artifact Storage, Alexandria Flora
Undergraduate Honors Thesis Collection
Many materials used for storage of museum artifacts have been found to cause damage to the items either through emitting harmful volatile gases or through direct contact. Harmful storage techniques can cause corrosion, discoloration, or deterioration of priceless artifacts. Museum enclosures made of hardwoods have been shown to emit acetic acid vapors that cause damage to the items being stored. In the present study, a review of the effects of acetic acid damage on museum artifacts was performed, and an evolved gas analysis and titration method were used to quantify acetic acid in various hardwoods.
Substrate Specificity Of The Lipn Hydrolase From Mycobacterium Ulcerans, Stephanie Raynor
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
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.
Synthesis And Resolution Of A Substituted Dioxolane From Glycerol, Susannah Dawn Cox
Synthesis And Resolution Of A Substituted Dioxolane From Glycerol, Susannah Dawn Cox
Undergraduate Honors Thesis Collection
Glycerol (Figure 1) is one of the major byproducts in the manufacturing of biofuels. As the interest in biodiesel grows, production of glycerol will also increase. Investigating glycerol's potential as a chemical feedstock could lead to the discovery of new uses for this byproduct created from biofuel production. By developing pathways to use glycerol as a starting material and as a solvent we will be able to synthesize other chemically relevant compounds.
Amino Acid Methyl Ester Chiral Ionic Liquids: A Concentration Study, Christopher J. Brown
Amino Acid Methyl Ester Chiral Ionic Liquids: A Concentration Study, Christopher J. Brown
Undergraduate Honors Thesis Collection
This project will investigate novel amino acid methyl ester chiral ionic liquids and determine how increased concentration of lanthanide solute and changes in size of counter ions tetramethylammonium and tetrabutylammonium affects interaction between the ionic liquid and the fluorescent lanthanide solute. Both concentration dependence and temperature dependence were discovered. The chiral ionic liquid [L-prolineCl][TfiN] reacted uniquely to the change in concentration.
Thermal Denaturation Of Mycobacterium Tuberculosis Protein Rv0045c Monitored By Intrinsic Tryptophan Fluorescence, Lindsey Renee Drake
Thermal Denaturation Of Mycobacterium Tuberculosis Protein Rv0045c Monitored By Intrinsic Tryptophan Fluorescence, Lindsey Renee Drake
Undergraduate Honors Thesis Collection
The aim of my project was to use intrinsic tryptophan fluorescence to monitor the denaturation pathway of a protein, specifically the Mycobacterium tuberculosis enzyme Rv0045c. The larger scientific goal and inspiration for this honors thesis was to use the amino acid residues of a protein to map it's unfolding by thermal denaturation.
Adding Gas Chromatography-Mass Spectrometry Data To A Melting Point And Thin-Layer Chromatography Laboratory, Adam M. Azman, Julie A. Barrett, Megan Darragh, John J. Esteb
Adding Gas Chromatography-Mass Spectrometry Data To A Melting Point And Thin-Layer Chromatography Laboratory, Adam M. Azman, Julie A. Barrett, Megan Darragh, John J. Esteb
Scholarship and Professional Work - LAS
The addition of gas chromatography–mass spectrometry (GC–MS) data interpretation to a thin-layer chromatography (TLC) and melting point (mp) laboratory for an introductory organic course is described.
Chiral Recognition In Amino Acid And Peptide Based Chiral Ionic Liquids, Daniel Mccray Kroupa
Chiral Recognition In Amino Acid And Peptide Based Chiral Ionic Liquids, Daniel Mccray Kroupa
Undergraduate Honors Thesis Collection
In this study, amino acid and peptide based chiral ionic liquids (ILs) were prepared and their chiral recognition ability probed using circularly polarized luminescence (CPL) spectroscopy. Potential applications of amino acid and peptide based chiral ILs include asymmetric synthesis and chiral resolution. The amino acid based chiral ILs under study were prepared from amino acid methyl ester cations and bis(trifluoromethane)sulfonamide ([TF2ND anions, specifically L-alanine methyl ester, D-alanine methyl ester, L-Ieucine methyl ester, and L-proline methyl ester. Cationic peptide ILs were prepared from L-alanyl glycine methyl ester cations and [TF2Nr anions and anionic peptide based ILs were prepared from tetrabutylammonium ([TBAt) …
Characterization Of Esterase Activity From The Bacteria, Francisella Tularensis, The Causative Agent Of Tularemia, Leigh Anna Weston
Characterization Of Esterase Activity From The Bacteria, Francisella Tularensis, The Causative Agent Of Tularemia, Leigh Anna Weston
Undergraduate Honors Thesis Collection
Francisella tularensis is the bacteria responsible for causing the disease tularemia and is listed as one of the top three-biowarfare agents. Among the proteins essential to the virulence and infectivity of F.tularensis are multiple esterases, which are enzymes that break down various ester, thioester, and amide bonds. In this project, the catalytic activity, substrate speci fi city, and structure of a putative esterase from F.tularensis was studied. Latent fluorophores based on the molecule, fluorescein, were unmasked by the enzymatic activity of the esterase and the increase in fluorescence was measured over time to determine how well the e tcrase recognized …
Chiral Recognition Study Of A Bimolecular Process In Amino Acid Chiral Ionic Liquids, Laurel Millikan Heckman
Chiral Recognition Study Of A Bimolecular Process In Amino Acid Chiral Ionic Liquids, Laurel Millikan Heckman
Undergraduate Honors Thesis Collection
In this study, chiral ionic liquid (CIL) solvents were prepared and tested for their chiral discrimination ability by probing with luminescence quenching. The CIL's were also tested for their impurities, viscosity and density. These experiments will help to determine the ability of CIL's to act as solvents in asymmetric catalysis. The chiral ionic liquids in this study were composed of amino acid methyl ester cations and bis(trifluoromethane) sulfonimide or bistri flimide anions (i.e. I-alanine methyl ester bistriflimid e, d-alanine methyl ester bistr iflim ide and I-leuci ne methyl ester bistriflimde). Circularly polarized luminescence (CPL) and its quenching in the chiral …
Development Of A Green Method For Amide Synthesis, Megan Ruth Darragh
Development Of A Green Method For Amide Synthesis, Megan Ruth Darragh
Undergraduate Honors Thesis Collection
The aim of this work was to determine the scope and limitations of using microwave technology, solvent-free conditions and green chemistry-applicable solid supports for amide synthesis. We hypothesize that the method developed by Comerford et al [12] may be applicable to other solid support systems already in use (silica, fly ash, and alumina), and that combined with the use of microwave technology, green and efficient synthesis of varied amides and other dehydration reaction products may be possible. These methods should show application to undergraduate, organic chemistry laboratories as well as large-scale production laboratories.
Technology For The Organic Chemist: Three Exploratory Modules, John J. Esteb, Luanne M. Mcnulty, John Magers, Paul Morgan
Technology For The Organic Chemist: Three Exploratory Modules, John J. Esteb, Luanne M. Mcnulty, John Magers, Paul Morgan
Scholarship and Professional Work - LAS
The ability to use computer-based technology is an essential skill set for students majoring in chemistry. This exercise details the introduction of appropriate uses for this technology in the organic chemistry series. The incorporation of chemically appropriate online resources (module 1), scientific databases (module 2), and the use of a chemical drawing program (module 3) are detailed here.
Solid Supported Synthesis Of Secondary Amines Via Staudinger And Microwave Aza-Wittig Reactions, Kyle Thomas Holsinger
Solid Supported Synthesis Of Secondary Amines Via Staudinger And Microwave Aza-Wittig Reactions, Kyle Thomas Holsinger
Undergraduate Honors Thesis Collection
Amine bond formation is a major topic in organic chemistry and is widely applied to the formation of medicinal compounds. Current studies have analyzed the benefits of microwave irradiation and solid supported reagents in order to improve reaction conditions and both synthetic and environmental costs. In the synthesis of amines, we investigate the combined use of microwave irradiation and solid supported reagents in the aza-Wittig and reductive amination reaction.
Solid Phase Amide Synthesis Using Staudinger-Vilarrasa Coupling And Microwave Irradiation, Ryan Patrick Schmidtz
Solid Phase Amide Synthesis Using Staudinger-Vilarrasa Coupling And Microwave Irradiation, Ryan Patrick Schmidtz
Undergraduate Honors Thesis Collection
Amide bond formation is an already well documented area of organic chemistry, and is very useful in its application in medicine and pharmaceuticals. However, current methods have not been investigated with regards to optimization of reaction times, solvents, and energy sources. In addition, current methods also utilize toxic solvents to cleave the peptide from the solid phase resin. In our study, we combine the Staudinger and Vilarrasa coupling reactions with microwave irradiation to develop and optimize the synthesis of amide bonds through the use of a solid support. Instead of attaching the peptide to the solid support, our amide bond …
Liquid Carbon Dioxide Extraction Of Various Food Flavors: Evaluation And Analysis, Deven Lee Shinholt
Liquid Carbon Dioxide Extraction Of Various Food Flavors: Evaluation And Analysis, Deven Lee Shinholt
Undergraduate Honors Thesis Collection
Sub- and supercritical carbon dioxide has been utilized as an extraction solvent for a variety of natural compounds. This requires the use of specialized high-pressure vessels. It was reported recently that common laboratory apparatus (centrifuge tubes) could be utilized in liquid carbon dioxide extractions obviating the need for specialized equipment. Various herbs and spices (including orange, lemon, lime, and grapefruit zest, oregano, rosemary, sage, spearmint, nutmeg, black peppercorns, cloves, caraway seeds, and vanilla beans) were used as substrates for liquid carbon dioxide extractions by this straightforward technique. The extracted oils, containing terpenes and terpenoids, were then analyzed through GC/MS. Liquid …
A Simple Sn2 Reaction For The Undergraduate Organic Laboratory, John J. Esteb
A Simple Sn2 Reaction For The Undergraduate Organic Laboratory, John J. Esteb
Scholarship and Professional Work - LAS
A simple procedure for the synthesis of n-butyl naphthyl ether is presented. This procedure represents an easy method for the production of an aryl ether by an SN2 reaction, uses ethanol as an environmentally friendly solvent, and does not require the use of a lachrymator. Product isolation is done by pouring the reaction mixture over ice and collecting the solid by suction filtration. Students typically recover from 7–95% of the ether.
A Flexible Solvolysis Experiment For The Undergraduate Organic Laboratory, John J. Esteb, John R. Magers, Luanne M. Mcnulty, Paul Morgan
A Flexible Solvolysis Experiment For The Undergraduate Organic Laboratory, John J. Esteb, John R. Magers, Luanne M. Mcnulty, Paul Morgan
Scholarship and Professional Work - LAS
A simple SN1 reaction is presented that uses bromotriphenylmethane and a range of oxygen-based nucleophiles including water and various alcohols. This procedure represents a process that affords easy isolation of solid products. Typical student yields ranged from 17–128% with the average yield of 50%. Students obtained products with a melting point range of 140 to 164 °C. This procedure offers multiple ways to adapt this experiment from a straight solvolysis reaction to a discovery-based experiment that explores the effect of nucleophile (for a more advanced group) or the method of product isolation.
A Comparison Of The Surface Adsorption Characteristics Of Reduced And Oxidized Cytochrome C On A Fused Silica Surface Via Attenuated Total Internal Reflection Spectroscopy, Casey M. Kraning
Undergraduate Honors Thesis Collection
No abstract provided.
Adsorption Studies Of Cytochrome C On A Silica Nanoparticle Surface, Carrie Ann Hedge
Adsorption Studies Of Cytochrome C On A Silica Nanoparticle Surface, Carrie Ann Hedge
Undergraduate Honors Thesis Collection
This honors thesis investigated the conformational changes in cytochrome c when it is adsorbed to silica nanoparticle surfaces before denaturant as well as when it is exposed to denaturant and then allowed to adsorb to silica nanoparticles.
Nontraditional Synthesis Of Organometallic Compounds And Allylic Alcohols, Andrew J. Hesse
Nontraditional Synthesis Of Organometallic Compounds And Allylic Alcohols, Andrew J. Hesse
Undergraduate Honors Thesis Collection
One of the central dogmas of chemistry is the use of convection heating to increase rate and yields of reactions. However, other methods for the impartation of energy do exist. Microwave irradiation uses high power waves to directly excite molecule into higher energy states. This speeds up the kinetics of the reaction and thermodynamically favorable products are formed at a higher rate. This project successfully uses microwave irradiation to perform organometallic syntheses of iron based compounds such as ferrocene and iron diene tricarbonyls. Another alternative method involves using mechanical energy as a substitute for thermal energy. By rapidly colliding reactants …
Projects That Assist With Content In A Traditional Organic Chemistry Course, John J. Esteb, John R. Magers, Luanne Mcnulty, Anne M. Wilson
Projects That Assist With Content In A Traditional Organic Chemistry Course, John J. Esteb, John R. Magers, Luanne Mcnulty, Anne M. Wilson
Scholarship and Professional Work - LAS
Projects that engage undergraduate students in content-based courses, such as organic chemistry, must relate to the material and provide useful tools for the divergent needs of the students. There are few examples of these types of projects in the literature. Herein, we describe two projects, the reaction notebook and the end-of-semester synthesis activity. Each project is designed to stimulate student ownership of the material and leads to engagement with the content of the course.
A Solvent-Free Baeyer–Villiger Lactonization For The Undergraduate Organic Laboratory: Synthesis Of Γ-T-Butyl-Ε-Caprolactone, John J. Esteb, James N. Hohman, Diana E. Schladaminger, Anne M. Wilson
A Solvent-Free Baeyer–Villiger Lactonization For The Undergraduate Organic Laboratory: Synthesis Of Γ-T-Butyl-Ε-Caprolactone, John J. Esteb, James N. Hohman, Diana E. Schladaminger, Anne M. Wilson
Scholarship and Professional Work - LAS
We present an experiment involving the Baeyer–Villiger oxidation reactionfor a first-year organic chemistry class. The Baeyer–Villiger reactionprovides an efficient method to convert ketones to esters or lactones. Most organictextbooks cover the Baeyer–Villiger reaction but owing to a lack of suitableexperiments, students seldom get to explore the reaction in the undergraduateteaching laboratory. In this experiment, m-chloroperoxybenzoic acid(m-CPBA) and4-tert-butylcyclohexanone are mixed together for 30 minutes under solvent-freeconditions to produce γ-t-butyl-ε-caprolactone in 95%yield. The solvent-free nature of this procedure greatly limits the quantityof waste generated by students and keeps costs low by removing the need for solvent.
Solvent-Free Conversion Of Alpha-Naphthaldehyde To 1-Naphthoic Acid And 1-Naphthalenemethanol: Application Of The Cannizzaro Reaction, John J. Esteb, Keith M. Glogorich, Stacey A. O'Reilly
Solvent-Free Conversion Of Alpha-Naphthaldehyde To 1-Naphthoic Acid And 1-Naphthalenemethanol: Application Of The Cannizzaro Reaction, John J. Esteb, Keith M. Glogorich, Stacey A. O'Reilly
Scholarship and Professional Work - LAS
The Cannizzaro reaction is routinely covered in organic textbooks, but owing to the shortage of suitable procedures for the undergraduate teaching laboratory, this reaction is seldom performed in a first-year organic chemistry class. In this experiment, powdered potassium hydroxide and α-naphthaldehyde are heated under solvent-free conditions to produce 1-naphthoic acid and 1-naphthalenemethanol in 86% and 79% yields, respectively. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to the typical solvent-based method of preparation. Note:Link is to the article in a subscription database available to users affiliated with Butler University. Appropriate login information …
Simple Epoxide Formation For The Organic Laboratory Using Oxone, John J. Esteb
Simple Epoxide Formation For The Organic Laboratory Using Oxone, John J. Esteb
Scholarship and Professional Work - LAS
We present an epoxide formation experiment for a second-semester organic chemistry laboratory. This oxidation utilizes Oxone, a commercially available oxidizing agent, in the industrially relevant process of epoxide formation. The oxidant performing the oxidation is dimethyldioxirane, which is formed in situ. This experiment demonstrates a simple synthesis of an epoxide and formation of a secondary oxidizing agent.
Cautionary Comments (Author Response), John J. Esteb, Anne M. Wilson
Cautionary Comments (Author Response), John J. Esteb, Anne M. Wilson
Scholarship and Professional Work - LAS
Reply to concerns about a safety factor in the paper, “A Solvent-Free Oxidation of Alcohols in an Organic Laboratory."
A Solvent-Free Oxidation Of Alcohols In An Organic Laboratory, John J. Esteb, Michael W. Schelle, Anne N. Wilson
A Solvent-Free Oxidation Of Alcohols In An Organic Laboratory, John J. Esteb, Michael W. Schelle, Anne N. Wilson
Scholarship and Professional Work - LAS
An oxidation experiment for a first-year organic chemistry class is presented. This oxidation utilizes a solid mixture of CuSO4•5H2O and KMnO4 prepared by mortar and pestle. The oxidations take place under solvent-free conditions and near quantitative yields are obtained for the reactions. Thin-layer chromatography is used to monitor the progress of the reaction. This experiment provides for the simple oxidation of a secondary alcohol to a ketone using a relatively nontoxic oxidizing agent under solvent-free conditions.
A Solvent-Free Claisen Condensation Reaction For The Organic Laboratory, John J. Esteb, Matthew B. Stockton
A Solvent-Free Claisen Condensation Reaction For The Organic Laboratory, John J. Esteb, Matthew B. Stockton
Scholarship and Professional Work - LAS
An experiment involving the Claisen condensation reaction for a first-year organic chemistry laboratory is presented. Claisen condensations are routinely covered in organic textbooks but owing to the long reaction times required to reach equilibrium in solution they are seldom explored in the undergraduate teaching laboratory. In this experiment, potassium tert-butoxide and ethyl phenylacetate are heated to 100 °C for 30 minutes under solvent-free conditions to produce 2,4-diphenyl acetoacetate in 80% yield. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to typical carbonyl condensation experiments.