Research Experiences to Enhance Learning

Project Publications

"A Research Project in the Organic Instructional Laboratory Involving the Suzuki-Miyaura Cross Coupling Reaction", Michael Novak, Yue-Ting Wang, Michael W. Ambrogio, Christopher A. Chan, Heather E. Davis, Kristin S. Goodwin, Melinda A. Hadley, Caitlin M. Hall, Alison M. Herrick, Alexander S. Ivanov, Christina M. Mueller, Jane J. Oh, Randal J. Soukup, Thomas J. Sullivan, and Andrew M. Todd, The Chemical Educator, accepted in press Sept. 2007. (additional materials)

Abstract:  

In the second semester majors’ organic laboratory course at Miami, students are introduced to a research project based on the Suzuki-Miyaura cross coupling reaction. Students, working in 4-6 person research groups, generate a research proposal, perform the independent research work, evaluate their results, and write a journal-style formal report summarizing their research. The student proposals are based on the extension of a published “green” version of the reaction that employs an entirely aqueous reaction solvent, and the easily recovered, and non-toxic Pd/C catalyst. In the two years that the project has been used 10 different student research groups have submitted proposals and performed research work in this project. Eight of ten projects led to a successful coupling reaction. Representative results from three of these groups are reported as examples of the sophistication of projects that can be carried out by students at this level.

"Synthesis of a Sonogel-Carbon Modified Sensor Electrode with Titanium Oxide (TiO₂) to Detect Catechol in the Presence of Common Interferents by Voltammetric Studies", Lunsford, Suzanne, K., Yeary, A., Stinson, J., Choi, H., Dionysiou, D., Analytical Science Digital Library, entry 010045, 05/29/07.

Abstract:  

This experiment was part of an Analytical/Instrumental Analysis course. It requires the synthesis of a sonogel-carbon electrode (SGC) modified with a TiO2 sol-gel and heated at high temperatures. The electrochemical response of the synthesized SGC/TiO2 electrode was compared to that of an unmodified sonogel-carbon electrode to detect catechol (catecholamines). The design of the experiment encourages some choices to be made by the student, although the sol-gel syntheses are recipe driven. The students were required to determine if the modified electrode showed marked enhanced detection of catechol in the presence of ascorbic acid, compared to an electrochemically prepared conducting poly (3-methylthiophene) electrode in the detection of catechol over several scans. The students gain electrochemical instrumentation skills and implement them by studying reduction-oxidation states of catechol in the presence of ascorbic acid.

"Dinuclear Lanthanide(III) Complexes Containing β-diketonate Terminal Ligands Bridged by a 2,2'-bipyrimidine.", Deepika D'Cunha, Daniel Collins, Gregory Richards, Gilford S. Vincent, and Shawn Swavey. Inorganic Chemistry Communications, Vol. 9(10), Oct. 2006, pp. 979-981.

Abstract:  

Reactions of lanthanide(III) (Ln^III) salts with the polyazine bridging ligand 2,2'-bipyrimidine (bpm) and β-diketonate terminal ligands yield 16 new monometallic and bimetallic complexes of the form Ln(tl)₃bpm and [Ln(tl)₃]₂bpm respectively, where tl = terminal ligand. Formation of the dinuclear complex is governed by the size of the lanthanide metal and the type of terminal ligand. The smallest Ln^III metals form dinuclear complexes when the terminal ligand consists of an aromatic and a fluoro group. The largest Ln^III metals (Pr and Nd) form only mononuclear complexes with the bpm bridging ligands regardless of the terminal ligand. The electronic spectra of the complexes is dominated by the π → π* transitions associated with the terminal ligand and the emission spectra are due to 4f–4f lanthanide transitions.

"Electrochemistry and Detection of Organic and Biological Molecules Such as Catechol and Ascorbic Acid at Conducting Poly (2,2-bithiophene) Electrode", Lunsford, Suzanne K., Stinson, J., and Widera, J., Analytical Science Digital Library, entry 10041, 9/08/06.

Abstract:  

This paper describes an undergraduate laboratory for an electroanalytical chemistry course that can be used to supplement the teaching of oxidation and reduction reactions. The laboratory also introduces basic electrochemical techniques, instrumentation, and preparation of a conducting polymer film, poly (2,2-bithiophene), as a chemical sensor for the detection of an organic molecule catechu in the presence of a common interferent, ascorbic acid.

"Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity", Jeffrey A. Demaray, Jason E. Thuener, Matthew N. Dawson, Steven J. Sucheck, Bioorganic & Medicinal Chemistry Letters, 18 (2008) pp. 4868-4871.

Abstract:  

C-5-substituted triazole-oxazolidinones were synthesized using a bromide catalyzed cycloaddition between aryl isocyanates and epibromohydrin followed by a three-component Huisgen cycloaddition. The library of compounds was screened for antibacterial activity against Mycobacterium smegmatis ATCC 14468, Bacillus subtilis ATCC 6633, and Enterococcus faecalis ATCC 29212. Notably, the 3-(4-acetyl-phenyl)-5-(1H-1,2,3-triazol-1-yl)methyl)-oxazolidin-2-one (18) showed an MIC of 1 μg/mL against M. smegmatis ATCC 14468, fourfold lower than the MIC measured for isoniazid.

"Anomeric Selectivity in the Synthesis of Galloyl Esters of D-Glucose" Robert C. Binkley, Jessica C. Ziepfel, Klaus B. Himmeldirk (Ohio University, Department of Chemistry & Biochemistry, Clippinger Laboratories, Athens, OH 45701, USA) Carbohydrate Research, 344 (2009) pp. 237-239 .

Abstract:  

The anomeric selectivity of the ester formation between D-glucopyranose and gallic acid was investigated under a variety of conditions. A new protocol was established that allows performing the reaction under conditions where mutarotation is very slow. Highly α- or β-selective transformations are possible when starting with α- or β-D-glucopyranose, respectively. Due to the kinetic anomeric effect, a high α-selectivity is more difficult to achieve than a high β-selectivity. The new methodology presented in this article was compared with established procedures for the synthesis of allotannins. In addition to the advantages of a high yield and an easy purification protocol, the new procedure uniquely allows for a highly selective synthesis of α-products.