Organic Chemistry Commons^™

Towards Novel Alkaline Earth Metal Pyrazolates: Opportunities In Materials Chemistry, Michael G. Bagnall

Renée Crown University Honors Thesis Projects - All

Until recent years, the coordination chemistry of the alkaline earth metals remained relatively unexplored. Owing to the development of new synthetic methods and improved techniques for the exclusion of air and moisture, great progress has been made into our understanding of the alkaline earth metals and their compounds. These compounds are useful in a wide variety of applications, including as polymerization initiators, precursors for chemical vapor deposition (CVD) and in metal-organic frameworks (MOFs) for gas separation and storage. Current work in alkaline earth metal chemistry focuses on designing and tailoring ligand systems to expand their potential applications in materials chemistry. …

Rational Design And Synthesis Of Multifunctional Nanostructures For Biological And Medicinal Applications, Amy N. Otuonye

Renée Crown University Honors Thesis Projects - All

Mobile Composite Material (MCM-41) was modified by the addition of various functional groups, which increase the materials’ efficiency for an assortment of applications. Mesoporous materials have demonstrated to be capable of adsorbing and releasing of model drug molecules, rhodamine 6G and ibuprofen. Mesoporous silica materials functionalized with mercaptopropyltrimethoxysilane (MPTS), vinyltrimethoxysilane (VTS), aminopropyltrimethoxysilane (APTS), and N-(2-animoethyl)-3-aminopropyltriethoxysilane (AAPTS) were used to test the adsorption and release of rhodamine 6G (R6G) and ibuprofen. The vinyl and mercaptopropyl groups adsorbed and released more rhodamine 6G than the primary and secondary amine groups. The adsorption and release of ibuprofen was the opposite of the R6G …

Synthetic Studies Of Laulimalide Analogues, Ian Addison Mcalexander

All Graduate Theses and Dissertations, Spring 1920 to Summer 2023

Chapter 1 provides some background information on the disease area of cancer and current modes of treatment. Chemotherapy treatment is discussed with a focus on the major cellular targets for these drugs: DNA and microtubules. For each target, classes of active compounds are described along with their mode of action. The microtubule stabilizing agent laulimalide is introduced and a case is made for analogue synthesis.

Chapter 2 describes our first generation efforts toward synthesis of des-methyl laulimalide. The target compound is divided into a northern and southern fragment with the synthesis of each fragment described. The preparation of landmark intermediates …

Organocuprate Mediated Syntheses Of O, And N-Heterocycles, Fenghai Guo

All Dissertations

ABSTRACT
The δ-lactone moiety comprises structural subunits in a number of natural products. Highly substituted δ-lactones are important both in synthetic applications and also as naturally occurring compounds. We have reported a one-pot procedure for the synthesis of trans-4,5-disubstituted tetrahydropran-2-ones from 3-hydroxy-3,6-dihydropyran-2-one involving sequential cuprate mediated allylic substitution and 1,4-conjugate addition reactions. We have now examined the same protocol for synthesis of 4,5,6-trisubstituted δ-lactones.
The rich functionalities(i.e. the epoxide, olefin and ester functional groups) in ,δ-epoxy-α,β-enoates provide opportunities for SN2-epoxide opening, allylic substitution, and 1,4-conjugated addtion. The opening of the epoxide with AcCl, AcBr, and benzoyl chloride afforded the -acetoxy--halo-,-enoates …

1,2-Dimethyl-4,5-Diphenylbenzene Determined On A Bruker Smart X2s Benchtop Crystallographic System, Jonathan B. Briggs, Mikael D. Jazdzyk, Glen P. Miller

Chemistry

The title compound, C(20)H(18), has two crystallographically independent molecules in the asymmetric unit. The phenyl substituents of molecule A are twisted away from the plane defined by the central benzene ring by 131.8 (2) and -52.7 (3)degrees. The phenyl substituents of molecule B are twisted by -133.3 (2) and 50.9 (3)degrees. Each molecule is stabilized by a pair of intraMolecular C(aryl, sp(2))-H center dot center dot center dot pi interactions, as well as by several interMolecular C(methyl, sp(3))-H center dot center dot center dot pi interactions.

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 …

Controlled Assembly Of Rodlike Viruses With Polymers, Tao Li, Laying Wu, Nisaraporn Suthiwangcharoen, Michael A. Bruckman, Dayton Cash, Joan S. Hudson, Soumitra Ghoshroy, Qian Wang

Faculty Publications

A practical method to assemble rodlike tobacco mosaic virus and bacteriophage M13 with polymers was developed, which afforded a 3D core–shell composite with morphological control.

Biodiesel: Tomorrow's Fuel, Today's Solution, Roberto J. Molina, Racheal A. Persuad

Undergraduate Research Conference

Study of physical and chemical properties of biodiesel fuels derived from poultry and plant fats.

Stereospecific Enzyme Isolation From Carrots, Jacqueline Greer, Eileen Rigsby

Undergraduate Research Conference

No abstract provided.

Spectroscopic Studies Of Fluoranthene And 3-Nitrofluoranthene, Matthew Parks

Undergraduate Research Conference

Polycyclic aromatic hydrocarbons (PAHs) are known byproducts of anthropogenic sources including incomplete combustion of fossil fuels. They are known to be teratogenic, mutagenic and carcinogenic. This study investigated the spectral properties of fluoranthene and 3- nitrofluoranthene using NMR, UV-Vis and infrared techniques. The acquisition of spectral data provides a means to identify these compounds in mixtures and can be used which to develop model formulae for quantitation. A 2-D NMR method (HMQC ) was used for assigning 13C peaks. The infrared spectrum for 3-nitrofluoranthene showed characteristic strong absorption peaks at 1323 and 1516 cm-1 assigned to symmetric/asymmetric nitro stretches, respectively. …

Light-Regulated Sampling Of Protein Kinase Activity (Ii), Collaborative Project

Dyson College- Seidenberg School of CSIS : Collaborative Projects and Presentations

This entry adheres to the use of the quad chart template to provide a succinct description only of the current research project undertaken by the participants. It provides for the following information

1. Participants and Affiliations
2. Overall Project Goals
3. Illustrative picture
4. Specific research/artistic/pedagogic foci

Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition Of Catalytically Generated Zinc Acetylides To Aldehydes, C. Wade Downey, Brian D. Mahoney, Vincent R. Lipari

Chemistry Faculty Publications

In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.

Dispersal And Establishment Both Limit Colonization During Primary Succession On A Glacier Foreland, Chad C. Jones, Roger Del Moral

Botany Faculty Publications

Plant colonization can be limited by lack of seeds or by factors that reduce establishment. The role of seed limitation in community assembly is being increasingly recognized, but in early primary succession, establishment failure is still considered more important. We studied the factors limiting colonization on the foreland of Coleman Glacier, Washington, USA to determine the importance of seed and establishment limitation during primary succession. We also evaluated the effects of seed predation, drought and existing vegetation on establishment. We planted seeds of seven species into plots of four different ages and found evidence that both seed and establishment limitation …

Structural Determination Of The 5' Untranslated Regions Of Ire-Containing Mrnas, Chandra Sekhar Bathina

Theses, Dissertations and Capstones

The expression of ferritin and amyloid precursor protein (APP) is post-transcriptionally regulated by iron-regulating proteins via binding to a stem-loop structure known as an iron-responsive element in the 5’-untranslated region (5’UTR) of ferritin and APP mRNAs. In this study, we used atomic force microscopy (AFM) to visualize the conformation of the 5’UTRs of ferritin heavy chain (Ferritin-H), ferritin light chain (Ferritin-L), and APP mRNA transcripts from human and mouse, and determined the secondary RNA structures using selective 2’-hydroxyl acylation analyzed by primer extension (SHAPE). The AFM imaging did not provide high resolution structural information about these RNAs, whereas the SHAPE …

(+-)-3-Carboxy-2-(Imidazol-3-Ium-1-Yl)- Propanoate, Sara A. Reeb, Marlesa C. Shields, Kraig A. Wheeler

Faculty Research and Creative Activity

The title compound, C7H8N2O4, crystallizes as a zwitterion, with molecules organized into molecular sheets via carboxyl– carboxylate and N+—H_ _ _carboxylate contacts. These sheets are constructed from translationally related molecules that further link to neighboring motifs via _-stacking [centroid– centroid distance 3.504 (3) A ° ] and weak C—H_ _ _O contacts.

Development Of A Carbon-Carbon Sandwich Composite With A Cellulose, Matt Brown

Mahurin Honors College Capstone Experience/Thesis Projects

The development of a carbon-carbon sandwich composite with a cellulose derived core was developed and its properties investigated. This type of hybrid composite has never been made before. The goal was to combine the high temperature properties of carbon-carbon composites with the low weight of sandwich composites. In order to create a material with superior thermal properties and a high specific strength a carbon-carbon sandwich composite was developed utilizing a carbonized wood core. The composite was successfully constructed using an industrial grade carbon glue to hold two layers of carbon fiber weave on the top and bottom of the core. …

Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth(Iii) Bromide Catalyzed Synthesis Of Substituted Tetrahydroquinoline Derivatives, Ram Mohan, Jamie Rogers, Justin Ernat, Herbie Yung

Scholarship

The bismuth bromide catalyzed synthesis of a range of substituted tetrahydroquinoline derivatives via a three component coupling reaction between substituted anilines and enol ethers is reported. Bismuth compounds are attractive for use as catalysts because of their remarkably low toxicity. Bismuth bromide is relatively inexpensive and easy to handle, and hence preferable to other corrosive catalysts previously used for synthesis of tetrahydroquinoline derivatives.

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

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.

Bowl-Shaped Polyaromatic Hydrocarbons (Buckybowls) : Crystal Packing And Metal Binding Reactions, Alexander S. Filatov

Legacy Theses & Dissertations (2009 - 2024)

This work is a part of a broad program in our laboratory dedicated to the investigation of a new class of non-planar polyaromatic hydrocarbons that map onto the surfaces of fullerenes (and referred to as buckybowls). It focuses on the preparation of buckybowls, their molecular and solid state structures, and reactivity in metal binding reactions. For the first time, the structures of all available buckybowls have been analyzed using X-ray diffraction data collected in the course of this work, as well as data previously obtained in our group or reported by others (and dearchived from the Cambridge Structural Database). Forces …

Arrow Pushing In Organic Chemistry: An Easy Approach To Understanding Reaction Mechanisms (Book Review), Jeffrey H. Glans

Chemistry & Physics Faculty Publications

A book review by Jeffrey Glans.

Levy, Daniel E. Arrow Pushing in Organic Chemistry: An Easy Approach to Understanding Reaction Mechanisms. New York: Wiley, 2008.

ISBN 9780470171103

Preparation And Characterization Of Some Substituted Benzyl N-Nitrosocarbamates Containing An N-2-(Methylthio)Ethyl Or A Bis(2-Aminoethyl)Sulfide Functionality, Satya Venkata, Eric Shamo, Vladimir Benin

Chemistry Faculty Publications

The synthesis and characterization of some substituted benzyl N-nitrosocarbamates with an N-2-(methylthio)ethyl or a bis(2-aminoethyl)sulfide functionality is reported, as a part of a long-term goal to design and prepare novel photolabile structures that could be used as substances for controlled release of alkylating and/or crosslinking agents. The synthesis was accomplished by reaction of benzyl chloroformates with the corresponding amines, resulting in the preparation of carbamates. The latter were subsequently nitrosated, utilizing two different N-nitrosation methods, to yield the target structures.

Substituent Effect On The Electronic And Assembling Properties Of Asymmetric Phenazine Derivatives, Bin Cao

UNLV Theses, Dissertations, Professional Papers, and Capstones

Currently, one-dimensional (1-D) nanostructures have drawn much interest because of their potential applications for nanoscale optoelectronic devices. Self-assembly (SA) based on π-conjugated systems through various intermolecular interactions has been widely used to produce 1-D nanostructure. Morphology of the assembled structures can be modified by incorporating substituents, which provide additional secondary interactions. Meanwhile, those substituents also influence the electronic properties of the molecules. Previous studies have made little effort to systematically study subsistent effects on both electronic and SA properties.

The primary objective of this research is to generate controllable 1-D structures through SA, and to provide a fundamental understanding of …

Preliminary Development Of Quantitative Immunoassays For Mitochondrial Proteins, Adriann Hovey

Honors Program Theses

Mitochondria are medium-sized organelles in which most cellular metabolic reactions are carried out. In postmitotic cells that are aged or diseased, such as myocardial, skeletal, and brain cells, abnormally large mitochondria ("giant mitochondria") are often observed. Mitochondrial size and shape are controlled by mitochondrial fusion and fission and disruption of this process may lead to their abnormally large size (Nauratil, Terman, Arriaga, 2008). These giant mitochondria exhibit variations from normal metabolism and altered membrane potentials (Nauratil et al., 2008). An increased number of giant mitochondria may therefore disrupt cell function (Nauratil et al., 2008). This accumulation may result either from …

Partial Ion Yield Sspectroscopy Around The Cl 2p And C 1s Ionization Thresholds In Cf3cl, D. Ceolin, Maria Novella Piancastelli, Wayne C. Stolte, Dennis W. Lindle

Chemistry and Biochemistry Faculty Research

We present a partial ion yield experiment on freon 13, CF₃Cl, excited in the vicinity of the C 1s and Cl 2p ionization thresholds. We have collected a large amount of cationic fragments and a few anionic fragments at both edges. We have observed a strong intensity dependence of Rydberg transitions with ion fragment size for the CF_nCl⁺ and CF_n⁺/F⁺ (n=0–3) series at both the Cl 2p and C 1s ionization edges. Selectivity in the fragmentation processes involving the C–Cl and C–F bonds are highlighted by the intensities of the C …

Microwave Assisted Solid-Supported Organic Synthesis: A Novel Methodology To Obtain 2,3-Disubstituted-1,4-Naphthoquinones, Israel Garcia-Martinez

Open Access Theses & Dissertations

This research focuses on the combinatorial solid phase organic synthesis (SPOS) of different bioactive compounds utilizing transition metal mediated reactions via microwave assisted organic synthesis (MAOS).

A microwave-assisted solid-supported Dötz benzannulation of chromium Fischer carbene complexes with various alkynes has been reported. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1,4-naphthoquinone derivatives in good to moderate yields with high purities. We demonstrated that solid phase organic synthesis of naphthoquinones via conventional heating is limited due to their long reaction times and high temperatures. The products decompose leading to low yields and purities.2 Microwave assisted synthesis of these naphthoquinones will …

Design, Synthesis And Study Of The Bridged And Cofacially-Arrayed Poly-P-Phenylene Molecular Wires, Matthew J. Modjewski

Master's Theses (2009 -)

Two novel series of bridged and cofacially-arrayed poly-p-phenylenes have been designed synthesized and studied. The bridged poly-p-phenylenes have been synthesized from a readily available diacetylenic precursor utilizing three high yielding steps, and their structures were determined by 1H/13C NMR spectroscopy as well as X-ray crystallography. The racemization barrier between the two atropoisomers was found to be ~12 Kcal mol-1; the versatility of the synthesis employed was extended to synthesis a triply bridged tetra-p-phenylene and a quadruply bridged penta-p-phenylene.

The cofacially-arrayed poly-p-phenylenes have shown that the X-ray crystal structures of the neutral compounds are largely dominated by C-H--π-interactions interactions while the …

Generation Of Novel Pikromycin Antibiotic Products Through Mutasynthesis, Shuchi Gupta, Venkatraman Lakshmanan, Beom Seok Kim, Robert Fecik, Kevin A. Reynolds

Chemistry Faculty Publications and Presentations

Mutasynthesis in pikromycin PKS: The amenability of pikromycin polyketide synthase to mutational biosynthesis has been demonstrated. A natural triketide and its analogues, activated as N-acetyl-cysteamine thioesters, were synthesized and fed to a pikAI-deleted strain; this led to the production of new antibiotics. A vinyl analogue was found to have better antibacterial activity than pikromycin.

Controlled Functionalization Of Crystalline Polyolefins And Their Application In Soluble Polymer Support, Jihoon Shin

UNLV Theses, Dissertations, Professional Papers, and Capstones

Functionalization of polyolefins has been recognized as a useful methodology for the generation of new materials with a wide range of applications. Recently, crystalline or semi-crystalline polyolefins have drawn increasing attention in both industrial and academic fields as one of the most interesting engineering plastics, due to their remarkable physical and mechanical properties. This dissertation describes: (1) novel methods for the direct postfunctionalization of crystalline polyolefins to introduce functionality, (2) characterizations for the functionalized polymers to analyze their structures, molecular-weight properties, thermal properties, and hydrophilicity, and (3) an application of the modified crystalline polystyrene as a soluble polymer support for …

Towards The Design And Syntheses Of Novel Triads Comprising Single Robson-Type Macrocyclic Dicopper(Ii) Cores Flanked By Two Terminal Polypyridyl Ruthenium(Ii) Complexes., Leslie Shane Moody

Electronic Theses and Dissertations

Progress toward the syntheses of new tetranuclear bimetallic complexes of copper(II) and ruthenium(II) was realized. The designed triads comprise a central binuclear copper(II) complex with a tetraiminodiphenolate macrocyclic Robson-type compartmental ligand. In the envisioned complexes, the macrocyclic core is further functionalized by attachment of two polypyridyl ruthenium(II) complexes. A novel dibrominated dicopper(II) Robson complex was formed by the 2:2:2 condensation reaction of 4-bromo-2,6-diformylphenol and 1,3- diaminopropane with cupric chloride. Similarly, a new dibrominated dizinc(II) was synthesized from zinc tetrafluoroborate and the same diamine and dialdehyde. The new dicopper(II) complex did not heterocouple with borylated substrates under explored Suzuki reaction conditions. …