Chemistry Commons^™

The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Steven Shadwick

Scholarship

We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.

Is Hyperconjugation Responsible For The "Gauche Effect" In 1-Fluoropropane And Other 2-Substituted-1-Fluoroethanes?, Paul R. Rablen, R. W. Hoffman, D. A. Hrovat, W. T. Borden

Chemistry & Biochemistry Faculty Works

The energies and geometries of a series of 2-substituted-1-fluoroethanes were computed at the MP2/6-311++G**(6D)//MP2/6-31+G* level of theory for both the maxima and minima of the rotation about the C-C bond. The results did not support the predictions of a hyperconjugative model, that both 1,2-difluoroethane and 1-chloro-2-fluoroethane would strongly prefer a gauche conformation, and that 1-fluoro-2-silylethane would strongly prefer an anti conformation. The existence of competing electrostatic interactions between the fluorine and the substituents at C-2 was indicated by the detailed geometries of the gauche conformers and by the calculated sensitivity of the gauche-anti energy differences to the presence of a …

The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick

Ram S. Mohan

Media Coverage Of Epa's Draft Dioxin Reassessment Report, Sharon M. Friedman, Megan A. Fitzpatrick, Brenda P. Egolf

RISK: Health, Safety & Environment (1990-2002)

Using content analysis, the authors examine the utility of news media in democratic decision making.

The Discovery-Oriented Approach To Organic Chemistry 1. Nitration Of Unknown Organic Compounds. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Sonia Mcelveen, Kostas Gavardinas, Jean Stamberger

Scholarship

Nitration is one of the most fundamental reactions in organic chemistry. However, the majority of the nitration experiments found in the standard lab textbooks are of the "cookbook" variety and convey none of the excitement associated with discovery in experimental chemistry. We have developed two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. 13 C NMR spectroscopy is a powerful structure elucidation tool and yet not many examples of the use of 13C NMR spectroscopy in organic lab experiments can be found. The experiment involves nitration …

The Discovery-Oriented Approach To Organic Chemistry 1. Nitration Of Unknown Organic Compounds. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Sonia R. Mcelveen, Kostas Gavardinas, Jean A. Stamberger

Ram S. Mohan

[2,3:5,6]Dibenzo[2.2.2]Octa-2,5,7-Triene (C2/C) And [2,3:5,6]Dibenzo[2.2.2]Octa-2,5-Diene, Lary Burrows, John M. Masnovi, Ronald J. Baker

Chemistry Faculty Publications

Two barrelene homologs are reported. Strain in the bicyclic framework of [2,3:5,6]dibenzo[2.2.2]octa-2,5,7- triene, (I) (C16H12), which is manifest in the deviations from ideality of the bond angles in the central bicyclic ringoSyStem and compression of the double bond [1.312 (3)A], is reduced in the more saturated derivative, [2,3:5,6]dibenzo[2.2.2]octa-2,5-diene, (II) (CI6H14), with the corresponding single bond being 1.5380 (19)A. The formation of isomorphs of (I) in both chiral (C2) and achiral (C2/c) space groups has implications for asymmetric syntheses involving solid (I) which rely on a non-centrosymmetric space group.

The Cytotoxicity And Mode Of Action Of 2,3,4-Trisubstituted Pyrroles And Related Derivatives In Human Tmolt4 Leukemia Cells, John T. Gupton, B. S. Burham, B. D. Byrd, K. E. Krumpe, C. Stokes, J. Shuford, S. Winkle, T. Webb, A. E. Warren, C. R. Barnes, J. Henry, I. H. Hall

Chemistry Faculty Publications

4-Carbechoxy-l-methyl-2-phenacyl-3-phenylpyrrole (9), 4-carbethoxy-2-(4-methoxybcnzoyl)-3-(4-methoxyphcnyl)pyrrole (10) and 2-(4-methoxybenzoyl)-3,4-bis-(4-methoxyphenyl)pyrrole (11) proved to be potent cytotoxic agents against the growth of murine and human leukemias and lymphomas. Selective toxicity was demonstrated against the growth of solid tumors, e.g. human adenocarcinoma of the colon SW480 and ileum HCT-8, glioma U-87-MG, and rat UMR-106 osteosarcoma. A mode of action study in Tmolt₄ leukemia cells demonstrated that the agents inhibited de novo purine synthesis at the regulatory sites PRPP-amido transferase, IMP dehydrogenase as well as dihydrofolate reductase resulting in significant inhibition of DNA synthesis in 60 min. Other biochemical sites …

Oxidation Of Benzoins To Benzils Using Bismuth(Iii) Nitrate-Copper(Ii) Acetate, Ram Mohan, Steven Tymonko, Bryce Nattier

Scholarship

Benzoins are oxidized to benzils in excellent yields by 0.4 equivalents of Bi(NO3)3.5H20 and 4 mol% of Cu(OAc)23)3.5H20 is a stable, inexpensive, commercially available solid. The relatively low cost and low toxicity of bismuth(Ill) nitrate makes this procedure a particularly attractive method for oxidation of benzoins.

The Hofmann Rearrangement Using Household Bleach: Synthesis Of 3-Nitroaniline, Ram Mohan, Keith Monk

Scholarship

No abstract provided.

Cyclopropane Fatty Acid Expression In Plants, Katherine M. Schmid

Scholarship and Professional Work - LAS

Pants [sic] are transformed with a bacterial cyclopropane fatty acid synthase gene to produce lipids containing cyclopropane fatty acids. Using this technology dihydrosterculate is produced in oilseed crops such as rape.

The Hofmann Rearrangement Using Household Bleach: Synthesis Of 3-Nitroaniline, Ram S. Mohan, Keith A. Monk

Ram S. Mohan

No abstract provided.

Oxidation Of Benzoins To Benzils Using Bismuth(Iii) Nitrate-Copper(Ii) Acetate, Ram S. Mohan, Steven A. Tymonko, Bryce A. Nattier

Ram S. Mohan