Chemistry in Action!   Thursday, June 6, 2002
Gilbert Addition room 313, 1:30 - 3:30 pm.
Department of Chemistry, Oregon State University

Poster Abstracts for 2002.

2002 Authors: Andrews, Azadeh , Bilyeu , Blair , Chiu, Cruickshank, Frieh , Hashimoto, Hendy , Locke, Nguyen ,Root , Tavoloni
Voorhees .

01-2002.

PHOTOCHEMISTRY OF 4-CHLOROBENZOPHENONE. Veronica Chiu, Department of chemistry, Oregon State University-Corvallis, Oregon 97331

4-chlorobenzopinacol was formed qualitatively from 4-chlorobenzophenone by using sunlight. The melting point for 4-chlorobenzophenone was 70°C, whereas, the melting point for benzopinacol was 170.6°C. FTIR was used for quantitative study of the photoreduction of 4-chlorobenzophenone. The photoreduction quantum efficiency was determined to be 0.59.

02-2002.  Heavy Atom Effect FOR 4-BROMO-4'-FLUOROBENZOPHENONE. Becky Locke, Department of Chemistry, Oregon State University, Corvallis OR 97331.

There is a change in the phosphorescence lifetime for S0 ←T1 between polar and non-polar solvents accompanied by blue shifts for the nπ* and red shifts for the π π*.   The heavy atom effect is evident when comparing these parameters with several related benzophenones.

03-2002. QUANTITATIVE PHOTOREDUCTION OF 4-FLUOROBENZOPHENONE TO 4,4’-DIFLUOROBENZOPINACOL. B.J. Root, Department of Chemistry, Oregon State University-Corvallis, Oregon 97331.

4-fluorobenzophenone (4FB) readily reduces to 4,4’-difluoro-benzopinacol in ultraviolet (UV) light. Analysis in isopropyl alcohol by FTIR spectroscopy revealed a linear relationship between the amount of 4FB reduced and the amount of time it was exposed to UV light (350 nm) in a Rayonet reactor. The photoreduction efficiency, Φred, of 4FB was determined to be 0.455.

04-2002.  A STUDY OF THE PHOTOREDUCTION EFFICIENY OF 4-METHOXY-4'-METHYL BENZOPHENONE. Natalya Azadeh, Department of Chemistry, Oregon State University, Corvallis, OR 97331.

5 mL samples of an approximately 0.05 M solution were irradiated with UV light for different lengths of time and the concentration of the benzophenone was followed using information from IR spectra.  Using a previously determined calibration curve to convert peak areas to concentration units (M), a plot of benzophenone concentration (M) vs. photons (emitted from the UV lamp) was obtained. The slope of this plot is the photoreduction efficiency for 4-methoxy-4'-methylbenzophenone.

05-2002. ISOLATION AND STRUCTURE ELUCIDATION OF MORESBIOL FROM THE TROPICAL BROWN ALGA STYPOPODIUM SP. Simeon S. Andrews,775 SW 15th ST., Corvallis, Oregon, 97333

One new natural product, moresbiol, was isolated from the Pacific marine brown alga Stypopodium sp. Moresbiol was found to be lethal to 44% of brine shrimp at a concentration of 10ppm. The structure of moresbiol was found to be similar to taondiol, but having a five-membered carbocyclic ring adjacent to the aromatic ring, which is a novel arrangement. NMR data was used to solve the structure but was ambiguous as to relative and absolute stereochemistry.

06-2002. USE OF 13C NMR FOR CHARACTERIZATION OF 4-FLUORO-4'-METHYLBENZOPHENONE.  A. Tavoloni, Dept. of Chemistry, Oregon State University, Corvallis Or 97331.

Purity for a synthesized benzophenone was determine using H NMR and 13C NMR. The results of the H-NMR were inconclusive but the 13C NMR clearly showed impurities.

07-2002. SOLVENT STUDY OF 4-CHLORO-4'-ETHYLBENZOPHENONE.  Adam Hendy,  Dept. of Chemistry, Oregon State University, Corvallis Or 97331

On completing the solvent study for 4-chloro-4'-ethylbenzophenone a blue shift was observed for the more polar solvent for the n-pi* transition, along with a longer lifetime in the non-polar dilute solvent. For the pi-pi* transition a red shift was observed.

 08-2002. CHARACTERIZATION OF 4-CHLORO-4'-BROMOBENZOPHENONE BY NMR SPECTROSCOPY. Michinao Hashimoto,  Oregon State University, Department of Chemistry, Corvallis, OR  97331.

1H NMR and 13C NMR was utilized to confirm the purity and structure of 4-chloro-4'-bromobenzophenone that was synthesized. From the spectra obtained, it was concluded that the synthesized compound was actually pure 4-chloro-4'-bromobenzophenone. Also, the values of chemical shift were compared with those calculated from correlation tables, which reasonably concurred.

09-2002. Regiospecificity of the Friedel Crafts acylation.  Jeff Bilyeu,  Oregon State University, Department of Chemistry, Corvallis, Oregon 97331.

The Friedel Crafts acylation of fluorobenzene with fluorobenzoyl chloride in the presence of the AlCl3 catalyst produces exclusively para product. 19F NMR was implemented to prove the specificity of the formation of 4,4'-difluorobenzophenone.

10-2002. PHOSPHORESCENCE LIFETIME COMPARISON OF 4,4’-DIMETHOXYBENZOPHENONE IN METHYLCYCLOHEXANE AND EPA, Brian W Blair. Department of Chemistry, Oregon State University, Corvallis, Oregon 97331

The following poster is a comparison of the phosphorescence lifetimes of 4,4’-dimethoxybenzopheneon two solvents. Methylcyclohexane was used as a non-polar solvent and EPA was used as a polar solvent for this particular study.
4,4’-dimethoxybenzophenone produces two lifetimes when dissolved in methylcyclohexane and when dissolved in EPA only one lifetime can be detected.

11-2002. VIBRATIONAL SPECTRA OF 4, 4’-DIBROMOBENZOPHENONE.  John Frieh, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331.

Raman (3500-500 cm-1) and IR (4000-400 cm-1) spectra of solid 4, 4’-dibromobenzophenone were recorded. Complete assignments of the spectra were made and the type of symmetry of the vibration. Additionally, the percentage of carbon-13 present in the sample was quantitatively measured and the influence of bromine para substitution on the normal modes was investigated.

13-2002.  A Study of the Purity for A 4-chloro-4'-methylbenzophenone.   Steve Cruickshank,  Department of Chemistry, Oregon State University, Corvallis, Oregon 97331. 

Melting point tests on the “purified” product of a Friedel Crafts acylation indicated the presence of a contaminant. The identity of an unknown contaminate was discovered using 1H and 13C NMR and FTIR characterization techniques. The synthesis of 4-chloro-4’-methylbenzophenone (CMBP) included toluene as a reagent; consequently, it was considered as a possible contaminant.

14-2002. A QUALITATIVE STUDY OF SLOW PHOSPHORESCENCE DECAY VALUES FOR TWO GRADES OF 4-CHLORO-4'-PROPYLBENZOPHENONE IN METHYLCYCLOHEXANE (MCH) AND EPAAndrea Voorhees, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331.

Slow Phosphorescence Decay values were studied after qualitative confirmation (from NMR spectra) of the equivalence of the two grades of benzophenone crystals. Due to synthesis problems and a lack of publication on the compound of interest, some values necessary for the calculation of photophysical properties were estimated.