Chemistry Commons^™

Photo-Friedel-Crafts Acylation With Sunlight, Fernando De Leon^, Shizue Mito*

COURI Symposium Abstracts, Spring 2012

No abstract provided.

Enantioselective Biotransformation Of Prochiral Ketone Via Daucus Carota, Ryan Smith, Charlie Knox, Elizabeth Davis

Undergraduate Research Conference

Biotransformations of prochiral ketones can be performed using plant cells. The benefits of using plant cells include low cost, environmentally sound procedures compared to conventional chemical processes, and the stereospecific nature of the reaction.1,2 Benzofuran-2-yl methyl ketone was reduced to (- )-benzofuran-2-yl-ethanol after incubation with carrots in water. The reaction was enantioselective in that it produced the S-isomer as indicated by optical activity. Currently, attempts to isolate the carrot enzyme and antimicrobial studies of the (-)-benzofuran-2-yl-ethanol product are underway.

Zirconium Mediated One-Pot Synthesis Of Γ-Amino Acids From Carbon Dioxide, Diego A. Pedroza^, Shizue Mito*

COURI Symposium Abstracts, Spring 2012

No abstract provided.

Towards The Synthesis Of An Α-L-Rhamnose And Α-D-Galactose Containing Trisaccharide Epitope Related To Trypanosoma Cruzi, Merieme Khamsi ^, Katja Michael *

COURI Symposium Abstracts, Spring 2012

No abstract provided.

Synthesis, Structure, And Spectroscopic Properties Of Diphenyl Pyridine Amine Platinum (Ii) Complexes, Jacqueline Gamboa Varela^, Alejandro J. Metta-Magaña, Jose E. Núñez*

COURI Symposium Abstracts, Spring 2012

No abstract provided.

I, Synthesis Of Β-Sitosterol And Phytosterol Esters. Ii, New Methodology For Singlet Oxygen Generation From 1,1-Dihydroperoxides, Jiliang Hang

Department of Chemistry: Dissertations, Theses, and Student Research

Phytosterols are steroid compounds structurally similar with cholesterol and vary in the nature of carbon side chain. β-Sitosterol is commercially available in preparative amount only as mixtures with other phytosterols. New semipreparative synthesis of pure β-sitosterol and sidechain-modified phytosterols is discussed in this dissertation. This new synthesis is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. Preparation of phytosterol esters for cholesterol metabolism study is also discussed in this dissertation.

Singlet oxygen (¹O₂) is the lowest excited state …

Chemoselective Oxidation Of 6,13-Bis(Decylthio) Pentacene, Claire Eunhye Cho

Theses and Dissertations

Organic semiconductors present much potential for industrial use because of their possible low cost production, Pentacene and pentacene derivatives are promising candidates for organic semiconductor research since their ^-conjugated electronic structures possess small HOMO- LUMO gaps and high field effect mobility. Whereas there is much potential in devices made from pentacenes they do however undergo short lifetimes and poor processability due to photodegradation and poor solubility of pentacene. Previous research has shown that the pentacene lifetime and solubility can be enhanced by arylthio and alkylthio substituents placed on the pentacene backbone. For example 6,13-i?/s(decylthio)pentacene was one of the longest lived …

Synthesis And Theoretical Studies Of Pyridyl Fullerene Derivatives For Supramolecular Applications In Photovoltaic Systems, Robert Vina-Marrufo ^, Danisha M. Rivera-Nazario, Agustin Molina-Ontoria, Luis Echegoyen *

COURI Symposium Abstracts, Spring 2012

No abstract provided.

Rhodium-Catalyzed Hydroboration Of 1,1-Disubstituted Alkenes, Scott A. Pettibone

Department of Chemistry: Dissertations, Theses, and Student Research

Enantioselective rhodium-catalyzed hydroboration is becoming an increasingly important asymmetric transformation of alkenes based upon the utility of the organo boranate ester intermediate. The newly acquired asymmetric C-B bond can be converted to C-O, C-N, C-C bonds and the organo borante can be coupled to SP2 hybridized halogen bonds, all with retention of configuration. Catalyzed hydroboration of 1,1-disubstituted alkenes are an especially challenging substrate class for this enantioselective transformation. The difficulty for catalysts to distinguish between the two enantiotopic faces of the olefin is one of the major issues that have to be overcome to achieve a desirable level of enantioselectivity. …

Design, Synthesis And Study Of Polycyclic Aromatic Hydrocarbons And Their Cation Radicals, Tushar Navale

Dissertations (1934 -)

The unifying theme of most of optoelectronic devices revolves around the charge carrier mobility of the organic materials used in the conductive layers, which is a measure of how easily the electron/hole moves in a particular pi conjugated organic material. When pi conjugated materials are incorporated in these devices, molecules are generally layered in random orientation. Consequently, the efficiency of charge transport in the conducting layers of these devices is governed not only by the intramolecular electron/hole transport through the backbone of the molecule but also by the intermolecular electron/hole transport between the molecules and hence packing of these molecules …

Design And Synthesis Of Polycyclic Aromatic Hydrocarbons For Emission And Through-Space Charge Delocalization Studies, Vijay Vyas

Dissertations (1934 -)

Over the past decades, a variety of pi-conjugated organic materials have been explored as potential charge transport materials in conducting layers of photovoltaic devices. The performance of these devices critically depend on the efficiency with which the charge carriers (electrons and/or holes) move within the pi-conjugated materials present in their hole and electron conducting layers before their collection at the electrode. Hence, a large amount of research effort is devoted not only to the preparation of new pi-conjugated organic molecules for charge transport applications but also in understanding the nature of charge transport along the molecule (intra-chain) as well as …

Room Temperature Syntheses Of Entirely Diverse Substituted Β-Fluorofurans, Li Yan, Kraig A. Wheeler, Roman Dembinski

Faculty Research and Creative Activity

Synthesis of highly substituted 3-fluorofurans is reported. The sequence began with preparation of tertbutyldimethylsilyl alk-1-en-3-yn-1-yl ethers from 1,4-disubstituted alk-3-yn-1-ones. Subsequent fluorination of alkenynyl silyl ethers with Selectfluor gave 2-fluoroalk-3-yn-1-ones in almost quantitative yield. Subsequent 5-endo-dig cyclizations using chlorotriphenylphosphine gold(I)/silver trifluoromethanesulfonate (5/5 mol%), N-bromo- or N-iodosuccinimide and gold(I) chloride/zinc bromide (5/20 mol%), all at room temperature, provided a facile method for the generation of substituted 3-fluoro-, 3-bromo-4-fluoro-, and 3-fluoro-4-iodofurans in good yields. Also, 2,2-difluoroalk-3-yn-1-ones were prepared by fluorination of alk-3-yn-1-ones under organocatalytic conditions. The structures of (Z)-tertbutyldimethylsilyl but-1-en-3-yn-1-yl ether, 3-bromo-4-fluorofuran, and 3-fluoro-4-(phenylethynyl)furan were confirmed by X-ray crystallography.

Microarray Analysis As A Strategy To Identify And Characterize Glycome Regulatory, John F. Rakus

Chemistry Faculty Research

Glycosylation involves the post-translational addition of carbohydrates to protein molecules and is an intricate and indispensable biochemical process. Study of this complicated network of interactions is hindered by the lack of a coding template analogous to the genetic code, and by the vast structural complexity inherent to carbohydrate polymers. We use lectins (non-enzymatic carbohydrate-binding proteins of non-immunological origin) as microarray probes to identify carbohydrate features expressed on cellular surfaces. Specifically, we utilized lectin microarray technology to investigate the differences in carbohydrates expressed by the cell lines of the Nation Cancer Institute’s NCI-60 panel. Our investigation identified tissue-specific expression differences in …

Dalton, David R.: Foundations Of Organic Chemistry: Unity And Diversity Of Structures, Pathways & Reactions (Book Review), Jeffrey H. Glans

Chemistry & Physics Faculty Publications

Book review by Jeffrey Glans.

Dalton, David R. Foundations of Organic Chemistry: Unity and Diversity of Structures, Pathways & Reactions. Hoboken, NJ: Wiley, 2011.

ISBN 9780470479087

Synthesis, Characterization And Computational Study Of [4]Octamethylferrocenophane, Benjamin Mark Wilson

Theses, Dissertations and Capstones

This thesis reports the synthesis of an organic molecule, 1,4-bis(2,3,4,5-tetramethylcyclopentadienyl)butane by two different methods, in about 75% and 85% crude yield. Deprotonation of this molecule followed by reaction with FeCl2 generated the tethered ferrocene, [4]octamethylferrocenophane. Although the yield was low in the first attempt (2%), this molecule has been characterized through NMR spectroscopy, X-ray crystallography, electronic spectroscopy, elemental analysis, and decomposition temperature. A computational study was performed to determine the energy gap between each minimum energy structure. It was found that the energy barrier was not high enough to prevent a rapid interconversion between the two structures of minimum energy …

Incorporation Of The Actin-Myosin Biomolecular Motor System Into A Microfluidic Device, Rebecca Marie Ragland

Theses, Dissertations and Capstones

Recently, the field of bionanotechnology has sought to develop a device containing a biomolecular motor nano-cargo transport system. Among many applications, a device of this sort could be used to sort, purify, or detect specific molecules. In this work, an attempt was made to incorporate the actin-myosin biomolecular motor system into a microfluidic device constructed out of polydimethylsiloxane (PDMS) and glass. Methods for cleaning and functionalizing the glass surface of the device were optimized. After performing actin-myosin motility assays in a variety of PDMS/glass devices, it was determined that the oxygen permeability of PDMS limited the quality of motility that …

Linus Pauling: Scientist Of The 20th Century, Laura Ward

Natural Sciences Student Research Presentations

This poster describes the contributions scientist Linus Pauling made to the fields of chemistry and molecular biology, including his hybridization theory.

Deuterium Tracer Studies Of The Mechanism Of Cobalt Catalyzed Fischer-Tropsch Synthesis, Chunfen Jin

Online Theses and Dissertations

Since the Fischer-Tropsch (FT) catalytic polymerization reaction has been discovered in 1920s, many kinds of possible mechanisms have been reported. However, there is still debate because there is a lacking of experimental evidence to discriminate the validity of each mechanism. To define the mechanism of Fischer-Tropsch-Synthesis (FTS), we must define the C-C formation pathways as well as the structure of initiator species in the process, and finally provide an explanation in mechanistic detail as to how branched hydrocarbon compounds are formed in the reaction sequence.

In order to understand the cobalt catalyzed mechanism of FTS, we conducted H2/D2 switching and …

Structure-Reactivity Studies Of Simple 4-Hydroxyprolinamide Organocatalysts In The Asymmetric Michael Addition Reaction Of Aldehydes To Nitroolefins, Fintan Kelleher, John Watts, Lien Luu, Vickie Mckee, Ed Carey

Articles

A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% e.e. for syn). Furthermore, the use of low catalyst loadings (5 mol%) and a low aldehyde molar excess (1.5 equivalents) were achieved.

Polymers Used In Medicine: Common Types And Benefits Of Drug Delivery Systems, Camille Andrews

Natural Sciences Student Research Presentations

This poster describes the common types and benefits of drug delivery systems.

The Many Pharmaceutical Discoveries Of Gertrude B. Elion, Alayna Bonse

Natural Sciences Student Research Presentations

This poster discusses the contributions of Gertrude B. Elion to pharmaceutical science.

Synthesis Of Oligosaccharide Mimetics By The Desulfurative Rearrangement Of Allylic Disulfides And Stereoelectronic Influence Of C-O Bonds On C- And O-Glycosylation, Myriame Moume-Pymbock

Wayne State University Dissertations

This dissertation focuses on two different problems. The first part of this manuscript presents the application of a novel methodology to access the synthesis of oligosaccharide mimetics while the second part focuses on the study of the stereoelectronic effects of proximal C-O bonds in C- and O-glycosylation reactions.

The first chapter provides a brief overview of the important roles that oligosaccharides and glycoconjugates play in biological processes and sets out the major advances that have been made in the past few decades in the synthesis of such complex structures while bringing out the ongoing challenges and the limitations that impede …

Composition And Antimicrobial Activity Of The Essential Oil Of Hyssopus Seravschanicus Growing Wild In Tajikistan, Rachel M. Thompson, Prabodh Satyal

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

No abstract provided.

Natural Antiparasitic Coumarins: An In Silico Study, William R. Erwin

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

No abstract provided.

A Chemical Ecological Investigation Of The Allelophatic Potential Of Lamium Amplexcaule And Lamiun Purpureum, Chelsea D. Jones, Katherine E. Woods

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

No abstract provided.

Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram Mohan, Neil Baldwin, Anna Nord, Brendan O’Donnell

Scholarship

Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.

A Discovery-Oriented Approach To Solid-Phase Peptide Synthesis, Brian Brennan, Matthew Bockman, Christopher Miedema

Scholarship

In this discovery-oriented laboratory experiment, students use solid-phase synthesis techniques to construct a dipeptide containing an unknown amino acid. Following synthesis and cleavage from the polymeric support, electrospray ionization-mass spectrometry is employed to identify the unknown amino acid that was used in the peptide coupling. This experiment, performed in two, 3-h laboratory periods, provides an opportunity for students to learn the technique of solid-phase peptide synthesis and to critically evaluate data that they generate in the laboratory. The experiment is suitable for second-semester organic chemistry students as they learn methods for the formation of amide bonds or upper-level biochemistry students …

Synthesis And Flame Retardant Testing Of New Boronated And Phosphonated Aromatic Compounds, Vladimir Benin, Sravanthi Durganala, Alexander Morgan

Chemistry Faculty Publications

The present report describes the preparation and use of some dimethyl terephthalate derivatives in transition metal-catalyzed coupling reactions to produce new reactive flame retardants. Dimethyl iodoterephthalate and dimethyl 2,5-diiodoterephthalate were successfully employed in the preparation of phosphonic and boronic esters and acids. The latter were tested for heat release with a microcombustion calorimeter (ASTM D7309) to determine the potential for heat release reduction of these flame retardant molecules. The results showed that the addition of boronic or phosphonic acids greatly lowered the heat release, due to a condensed phase (char formation) mechanism. Adding ester groups to the boronic acids or …

Donor-Sigma-Acceptor (D-Sigma-A) Molecules With Perylenebisimide Acceptors Having Alkyl Or Peg Swallowtails With Sulfur Or Hydroxyl Anchors: Synthesis And Applications In Langmuir-Blodgett Films, Single Molecule Spectroscopy (Sms), G-Quadruplex Studies And Passivation Of Gold Nanoparticles, Rajesh Kota

Electronic Theses and Dissertations

Use of single molecules as electronic devices is presently considered a potential alternative to semiconductor-based nanoscale electronics. The ability to study a single molecule or a small group of molecules provides a great opportunity to build electronic devices at the molecular level. It is vital to understand the parameters that control the device properties such as molecular structure, conformation and arrangement at the surface. Ari Aviram and Mark A. Ratner proposed the construction of a single organic molecule as an organic rectifier. Donor-Sigma-Acceptor (D-?-A ) molecules, when arranged with a proper orientation as Langmuir-Blodgett (LB) films and fixed between two …

Isotopic Characterization Of Aerosol Organic Carbon Components Over The Eastern United States, Andrew S. Wozniak, James E. Bauer, Rebecca M. Dickhut, Xu Li, Ann P. Mcnichol

Chemistry & Biochemistry Faculty Publications

Carbon isotopic signatures (δ¹³C, Δ¹⁴C) of aerosol particulate matter total organic carbon (TOC) and operationally defined organic carbon (OC) components were measured in samples from two background sites in the eastern U.S. TOC and water-soluble OC (WSOC)δ¹³C values (−27 to −24‰) indicated predominantly terrestrial C₃ plant and fossil derived sources. Total solvent extracts (TSE) and their aliphatic, aromatic, and polar OC components were depleted in δ¹³C (−30 to −26‰) relative to TOC and WSOC. Δ¹⁴C signatures of aerosol TOC and TSE (−476 to +25‰) suggest variable fossil contributions (∼5–50%) …