Chemistry in Action!   Thursday, June 7
Gilbert Addition room 313, 1:30 - 3:30 pm.
Department of Chemistry, Oregon State University

Poster Abstracts for 2001.
Alphabetical List of Authors.

01-2001. ABSENCE OF BLUE-SHIFT IN UV SPECTROSCOPY OF 4-FLUOROBENZOPHENONE IN ISOPROPANOL. D.M. Volkov, Department of Chemistry, Oregon State University, Corvallis, OR 97331.

UV spectra for 4-fluorobenzophenone were obtained in both isopropanol and methylcyclohexane. The expected blue shift (caused by delocalization of electron density as a result of H-bonding to the carbonyl oxygen) was not observed. Strong H-bonding to fluorine could be the cause of this absence by withdrawal of electron density from the carbonyl. Results of the same type of study with the 4-chloro derivative support this conclusion.

02-2001. DETERMINATION OF PHOTOREDUCTION QUANTUM EFFICIENCY.  Ilanya V. Strauss, Department of Chemistry, Oregon State University, Corvallis, OR 97331.

The photoreduction quantum efficiency was determined through analysis of IR data of four diluted standards. A calibration curve was plotted using areas and concentrations. From the calibration curve and IR data of irradiated solutions, a plot of moles reacted and moles of photons was made. This data gives the quantum efficiency of the compound 4-methylbenzophenone.

03-2001. 4-BROMO-4’-METHYLBENZOPHENONE: THE PHILOSOPHER’S STONE. David Camoriano, Department of Chemistry, Oregon State University, Corvallis, OR 97331.

For centuries reputable chemists have been searching for that chemical agent capable of transmuting ordinary lead into precious gold. Failure to make any significant contributions to this promising field has caused a demise in the funding of such research. By fortuitous accident, I stumbled upon the philosopher’s stone while performing a spectroscopy experiment for my CH463 class. Isolation of golden 4-bromo-4’-methylbenzophenone crystals that phosphoresce clearly indicate the gold-converting properties of this substance.

04-2001. PHOSPHORESCENCE MEASUREMENTS OF 4-BROMO-4’METHYLBENZOPHENONE, David Camoriano, Department of Chemistry, Oregon State University, Corvallis, OR 97330.

Phosphorescence occurs when the population of a previously excited electronic singlet (S1) slowly reverts to its ground state (S0) via a transient, lower energy triplet state (T1). In the 4-bromo-4’-methylbenzophenone system, this corresponds to a p * n electronic transition in the carbonyl. Spectroscopic constants for the spin and symmetry forbidden T1 p * n S0 transition were calculated from the emission spectrum of this compound.

05-2001. QUANTITATIVE STUDY OF THE PHOTOREDUCTION OF 4-CHLORO-4'-ETHYL-BENZOPHENONE BY FTIR. Matt D. Reeves, Department of Chemistry, Oregon State University, Corvallis OR 97333.

Benzophenones are a class of compounds that have been extensively studied for their photoreduction to benzopinacols. This poster presents a quantitative study, by FTIR, of the photoreduction of 4-chloro-4'-ethyl benzophenone. The quantum efficiency of photoreduction was found to be 1.1.

06-2001. PHOTOREDUCTION OF 4,4'-DIFLUOROBENZOPHENONE TO BENZOPINACOL. Cristian V. Ion, Department of Chemistry, Oregon State University-Corvallis, 97331  

4,4’-difluorobenzophenone shows a high reduction efficiency to benzopinacol. A study of the change in the disubstituted benzophenone with time is presented that shows that 4,4’-difluorobenzophenone is 70 % efficient when starting from 4.5 % solution of disubstituted benzophenone in isopropanol. It can therefore be a good starting material for the synthesis of the substituted pinacol (1,1,2,2-tetrafluorophenyl-1,2-ethanediol) on a commercial basis.

07-2001. FRIEDEL CRAFTS ACYLATION OF ACID CHLORIDE WITH A MONOSUBSITUTED BENZENE, Derek J Hammill, Department of Chemistry, Oregon State University, Corvallis, OR 97331

Description of the steps and meanings of the Friedel Crafts reaction in the synthesis of a disubsituted benzophenone. Description details of how ortho, para directors affect the synthesis in the case where AlCl3 acts as a catalyst. A graphic display of the multi-step mechanism will also be included. Different substituents will also be addressed, including -Br, -Cl, -F, -OCH3, and -CH3.

08-2001. RAMAN AND INFRARED SPECTRSCOPY OF 2,4` AND 4,4`-DIMETHYLBENZOPHENOENE, Chun Y. Park, Department of Chemistry, Oregon State University, Corvallis, OR 97331

Infrared and Raman spectra were used to characterize 4,4'-dimethylbenzophenone and its isomer.  The infrared spectrum was used to find the characteristic of a ketone and Raman was used to find the characteristic of benzene.  The 4,4'dimethylbenzophenone gave : IR (KBr) nmax: 3039.6, 2922.1, 1652.6, 1606.4, 749.4 cm-1, and Raman nmax: 3065.1, 2925.9, 1643.8, 1604.1, 1217.5, 1144.2, 822.5, 631.8 cm-1.

09-2001. CONTAMINATION DURING THE SYNTHESIS OF 4-CHLORO-4'-METHOXYBENZOPHENONE. Amy E. Chan; Department of Chemistry, Oregon State University, Corvallis, OR 97331

Published journal articles concerning the synthesis of disubstituted benzophenones have dated back to nearly the beginning of the 1900's. Even so, trying to replicate these experiments do not always replicate the results. Every experiment has potential areas for contamination whether it be miscalculations, dirty glassware, or disruptions in the system, etc. This poster will explore the various avenues for this as well as possible solutions.

10-2001. PHOTOPHYSICS OF 4-FLUORO-4'-METHOXYBENZOPHENONE. Mac A. Wisdom, Department of Chemistry, Oregon State University, Corvallis, OR  97331

4-fluoro-4'-methoxybenzophenone was used in a series of photochemical experiments.  Excitation and emission experiments were conducted using a polar and nonpolar solvent.  Electronic transitions occur differently at different concentrations within this two solvent system.  My poster will examine the differences between the more dilute concentrations of the aformentioned benzophenone in ethanol and methylcyclohexane.  The main discussion will be differences in lifetime dealing with the pi-to-pi* transitions within the electronic structure of the molecule.

11-2001. THE THEORY AND APPLICATION OF VACUUM DISTILLATION. Lindsay A. Bader,Department of Chemistry, Oregon State University, Corvallis, 97331.

The theory behind vacuum distillation is quite simple. Create a vacuum and lower the pressure inside the aparatus. The lowered pressure lowers the boiling point of the solution of interest. This allows substances that would otherwise require a great deal of heating to reach such high boiling points, to be distilled in a normal laboratory setting. Vacuum distillation can be applied to pretty much any field of study. With some benefits being specific to water purification.

12-2001. HNMR SOLVENT STUDY FOR 4-BROMO-4'-CHLOROBENZOPHENONE. Rebecca Medina, Department of Chemistry, Oregon State University, Corvallis, 97331.

4-bromo-4'-chlorobenzophenone was synthesized by the Friedel Crafts acylation method. After recrystallization from ethanol, HNMR spectroscopy was utilized to confirm the structure of the benzophenone. Due to the overlapping of resonance signals for the two hydrogens adjacent to the bromine substituent (in CDCl3), additional HNMR spectra were run in differnent solvents (d-benzene, d-acetone, d-acetonitrile, and d-DMSO) to resolve those peaks. CNMR and HSQC were also taken to help confirm the structure.

13-2001. SYNTHESIS AND CHARACTERIZATION OF 4-FLUORO-4'-METHYLBENZOPHENONE. David C. Hartmann, Department of Chemistry, Oregon State University, Corvallis, OR 97331

A Friedel-Crafts acylation of 15.86 g of 4-fluorobenzoyl chloride with excess toluene yielded 49.63 g of wet 4-fluoro-4'-methylbenzophenone. The product was characterized and purity was confirmed with infrared spectroscopy, with nuclear magnetic resonance spectroscopy, and with a narrow melting range of 95.0-95.5 C.

14-2001.  PROTON NMR OF 4-BROMO-4'-FLUOROBENZOPHENONE. Jessie L. Hartford, Department of Chemistry, Oregon State University, Corvallis, OR 97331.

Analysis of the pronton NMR of the synthesized 4-bromo-4'-fluorobenzophenone reveals interesting results. The protons on the aromatic ring containing the bromine showed up as two strong peaks at approximately 7.2 and 7.58ppm. The protons on the aromatic ring with the fluorine were at approximately 7.1 and 7.75 ppm, however instead of being a strong peak as the bromine protons, they were a triplet of triplets. This is due to the large coupling constant between fluorine and the hydrogens. Fluorine is spin 1/2 like the protons. The coupling constant between fluorine and the meta hydrogens is 9 Hz, and the coupling constant between the fluorine and the ortho hydrogens is 6 Hz, the same as if it was two meta hydrogens coupled together.


A description of the mechanics involved with the photo reduction of benzophenone into the benzopinacol form and an analysis of the photo reducing properties of DCBP. This will involve a look at the quantitative analysis, as well as a macroscopic look at DCBP's photo-properties and an error analysis.

16-2001. QUALITATIVE QUANTUM EFFICIENCY OF PHOSPHORESCENCE OF 4-METHOXY BENZOPHENONE. B.G. Chan, Department of Chemistry, Oregon State University, Corvallis, OR 97331.

The phosphorescence quantum efficiency is determined by referencing the total integrated emission results for 4-methoxybenzophenone to the total integrated emission for ethanol and methylcyclohexane. It was found that the efficiency of phosphorescence in a non-polar solvent was 86.64% and in a polar solvent the efficiency dropped to 10.76%. The drop in efficiency was likely due to the hydrogen bonding between 4-methoxybenzophenone and the ethanol providing another pathway of energy relaxation.

17-2001. EFFECTS OF POLAR AND NON-POLAR SOLVENT ON WEAK AND STRONG PHOTOPHYSICAL TRANSITIONS IN 4-METHOXY-4’-METHYL-BENZOPHENONE. Jason A. Schindler, Department of Chemistry, Oregon State University, Corvallis, OR 97331

Samples of 1x10-4 M 4-methoxy-4’-methyl-benzophenone in ethanol and methylcyclohexane were analyzed by ultraviolet absorption. Special attention was paid to the photo-excitations associated with the carbonyl group and the ground to singlet (n p *) and singlet to singlet (p p *) excitations. The latter of the excitations were found to be strong oscillators (f = 0.5) whereas the former were found to be weaker oscillators (f = 0.005). The effect of the different solvents was evident by the disappearance of the weaker n p * transition in ethanol which can be explained by an overlapping wavelength shift in the UV spectra.

18-2001.  ACTIVITY OF 2,5-DIHYDROXYACETANILIDE EPOXIDASE II TOWARDS THE ALTERNATIVE SUBSTRACTS. Veronica Chiu, Scott Allen, and Kevin Gable, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331

(3-si,4-re)-2,5-Dihydroxyacetanilide epoxidase (DHAE I) and (3-re,4-si)-2,5-Dihydroxyacetanilide (DHAE I)and (3-re,4-si)-2,5-Dihydroxyacetanilide epoxidase(DHAE II)lead to production of enantiomeric products from the achiral substrate. DHAE II was isolated and purified in order to test the enzyme activity. Different alternative substracts were added to DHAE II to test the enzyme activity.

19-2001.  SOIL MICROBIAL POPULATION RESPONSE TO NITROGEN SATURATION. S.B. Bell (1), L. Watrud (2). (1) Department of Microbiology, Oregon State Univesity, Corvallis, Oregon 97331. (2) U.S. EPA, Western Ecology Division, Corvallis, Oregon 97333.

An increase in nitrogen (N) pollution from sources such as automobiles and agriculture is a major concern. To study the effects of high concentrations of N on forest systems, scientists from New Hamphshire Univeristy have added extreme concentrations of ammonium nitrate to hardwood and pine forest stands at Harvard Forest (Petersham, MA), since 1988. When soil microbial communities plated on various N substrates, a dramatic decrease in the biological activity was observed. High additions of N has also been associated with a significant decrease in pH.



Bader, L.A. 11-2001
Bell, S.B., Watrud L.19-2001
Camoriano, D. 04-2001 (03-2001, canceled)
Chan, A.E. 09-2001
Chan, B.G. 16-2001
Chiu, V., Allen, S., Gable, K. 18-2001
Hammill, D.J . 07-2001
Hartford, J.L. 14-2001
Hartmann, D.C. 13-2001
Ion, C.V. 06-2001
Medina, R. 12-2001
Mills, R.J. 15-2001
Park, C.Y. 08-2001
Reeves, M.D. 05-2001
Schindler, J.A. 17-2001
Strauss, I.V. 02-2001
Volkov, D.M.  01-2001
Wisdom, M.A. 10-2001