Chemistry in Action!   Thursday, June 2
Gilbert Addition room 313, 1:30 - 3:30 pm.
Department of Chemistry, Oregon State University

Poster Abstracts for 2004

Web Form for Submitting Poster Abstracts
Alphabetical list of authors

Experimental Chemistry II, CH 463 & 463H Poster Abstracts

01-2004.  PHOTOREDUCTION OF 4-METHOXYBENZOPHENONE. R.E. Holcomb, Undergraduate Chemistry, Oregon State University, Corvallis, Oregon 97331 

4-methoxybenzophenone undergoes a pinacol rearrangement when irradiated with UV light. The photoreduction quantum efficiency for 4-methoxybenzophenone was determined by FT-IR analysis of 4-methoxybenzphenone solutions irradiated at 350 nm for known amounts of time. The photoreduction product was characterized by a melting point determination and H-NMR.     

02-2004. SOLVENT INTERACTION OF 4-CHLORO-4'-ETHYLBENZOPHENONE. Gerrick E. Lindberg, Department of Chemistry, Oregon State University, Corvallis, Oregon, 97331.

UV excitation and emission spectroscopies are common tools in characterizing the electronic modes in a compound, but these spectra are dependent upon the polarity of the solvent. The more polar, EtOH, intermediate ,EPA, and more non-polar, methylcyclohexane, solvents were selected for an analysis of the wavelength shifts of the identifying peaks. This also provides information about the way that solvents interact with the analyte in solution. A polar solvent will cause excitation and emission to occur at wavelengths that are longer, blue shifted, compared to the more polar solvent because there is interaction between the solvent and the analyte.

03-2004.  PHOTOCHEMICAL REDUCTION OF 4-CHLORO-4'-METHOXYBENZOPHENONE TO 4,4'-DICHLORO-4,4'-DIMETHOXYBENZOPINACOL. Tony T. Tong, Department of Chemistry, Oregon State University, Corvallis, OR, 97331

Benzophenones are often synthesized and studied due to a unique ability to photoreduce to a benzopinacol. A disubstituted benzophenone, 4-chloro-4-methoxybenzophenone, was quantitatively reduced by UV irradiation. The quantum efficiency of the benzophenone was determined by varying the irradiation times and comparing the FTIR spectra to those of known concentrations.

04-2004.  PHOTOPHYSICAL CHARACTERIZATION OF 4-CHLORO-4'METHYLBENZOPHENONE.  Rona K. Nishikawa.  Department of Chemistry. Oregon State University, Corvallis, OR 97331-4003

Using UV absorption, excitation and emission spectroscopy to build  the Jablonski energy diagram for two sets of transitions. 

05-2004.  PHOTOCHEMISTRY OF 4-BROMOBENZOPHENONE. R.M. Hasson, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331

After synthesis, 4-bromobenzophenone is characterized by UV induced peaks. Grams 32 program was used to analyze the data gathered. Information is displayed in a Jablonski diagram. This compound also forms a benzopinacol when UV irradiated.

06-2004.  UV ABSORPTION SPECTROSCOPY OF 4-BROMO-4'-METHYLBENZOPHENONE IN POLAR AND NONPOLAR SOLVENTS.  L.W. O'Rourke, Department of Chemistry, Oregon State University, Oregon 97331

Although usually unseen within the absorption envelope in polar solvents, the distinct absorption of various vibrational levels found in the pistar <-- pi and pistar <-- n electronic transitions can be seen in nonpolar solvents.  This was demonstrated by obtaining two sets of spectra, one in EtOH and the other in methylcyclohexane.  These spectra, as well as the differences in the physical parameters they generated will be presented. 

07-2004. PHOTOREDUCTION OF 4-BROMO-4'-METHOXYBENZOPHENONE. Abdul Hackim, Department of Chemistry, Oregon State University, Corvallis, OR 97331

The object of this experiment was to determine the efficiency of the photochemical reduction of 4-bromo-4-methoxybenzophenone to the corresponding benzpinacol. Using a procedure involving a quantitative analysis of FTIR spectra, the photoreduction quantum efficiency of 4-bromo-4-methoxybenzophenone was determined to be 51.8% of that of unsubstituted benzophenone. This relative efficiency lends insight to the possible effects of substituent groups on the photoreduction process.


The photochemical conversion efficiency(phi)of 4,4'-dibromobenzophenone (DBBP) to the corresponding pinacol, 4,4'-dibromobenzopinacol (DBBC) was studied employing an analytical FTIR method.  The photoconversion was conducted in dichloromethane due to insolubility of the pure ketone in isopropanol.  The photoconversion was monitored with FTIR absorbance as a function of time and was analyzed using Beer's Law.  A calibration curve was constructed and a linear regression was performed on the four point curve to determine the rate of photoreduction.

09-2004. SYNTHESIS, PURIFICATION, CHARACTERIZATION AND PHOTOCHEMISTRY OF P-METHYLBENZOPHENONE. Rashelle A. Simmons, Department of Chemistry, Oregon State University-Corvallis, Oregon 97331

P-methylbenzophenone is synthesized from benzoyl chloride and toluene in CS2 solvent. Crystallization and purification is a fine art in that each time a water-ethanol mix was applied to the crude crystals, it became more difficult to isolate the pure white form. The 1H-NMR and 13C-NMR data indicate a pure product. Spectrophotometry is employed to produce Jablonski diagrams for transitions for npi* and pipi* revealing molecular vibrations.

10-2004.  EFFECTS OF POLAR SOLVENTS ON STABILIZING 4,4'-DIMETHOXYBENZOPHENONE IN A CHARGE TRANSFER DERIVATIVE.  Michael Herndon, Department of Chemistry, Oregon State University, Corvallis, Oregon 97330.

Benzophenone when containing methoxy groups for its substituents will be polarized to a charge transfer form due to the excitation (UV/light/hv) of one of the lone pairs on the oxygen of the methoxy group.  This polarized derivative will be stabilized in this form when kept in a polar solvent such as ethanol, but it will be allowed to return to its more favorable configuration when placed in a non-polar solvent such as methylcyclohexane.  This will be evident from the examination of these two forms in a UV study.

11-2004.  SOLVENT STUDY OF PHOTOPHYSICAL PARAMETERS FOR 4-METHYL-4'METHOXYBENZOPHENONE. E.H. Camp, Department of Chemistry, Oregon State University, Corvallis, OR 97331 

Excitation and emission wavelengths for 4-methyl-4'methoxybenzophenone were measured in ethanol and methylcyclohexane.  These wavelengths were found to be solvent dependent.  The lifetime of the triplet state was also measured and will be discussed.

12-2004.  Characterization and Solvent Study of 4,4'-DICHLOROBENZOPHENONE; Spencer P. Huff; Oregon State University 97331

After the synthesis of 4,4'-dichlorobenzophenone it was characterized with melting temperature, IR, and proton NMR. Once the NMR confirmed the the 2,4' isomer had been removed a solvent study was done on the DCBP using EtOH and methylcyclohexane (MCH). In the more polar solvent there was a shift to the higher energy level(EtOH) for the n-pi* and a shift to the lower energy level for the pi-pi*.





A substituted benzophenone can be photochemically reduced to its corresponding benzopinacol. The mechanism entails the triplet state benzophenone abstracting a hydrogen from the solvent (isopropyl alcohol) forming a benzhydrol radical, which dimerizes into the benzopinacol. IR and NMR spectra can be used to indicate if the benzopinacol has formed. The loss of a carbonyl peak and gain of an OH peak in the IR indicates benzopinacol formation. Proton NMR shows an upfield shift of the peaks of the pinacol due to the electron donating effects of the OH groups.

14-2004.  SYNTHESIS AND PHOTOREDUCTION OF 4-FLUOROBENZOPHENONE. Michael P. Donnelly,  Department of Chemistry, Oregon State University, Corvallis, OR  97331.

Given the unusual product formation that was last synthetically produced more than seventy years ago, it seems worth noting the differences between that synthesis and this modern one.  Though similar side products were found by the last team and this author most of the current methods of characterization were unavailable as of that writing.  Additionally the photoreduction efficiency of the molecule(~40%) will be discussed.

15-2004.  SYNTHESIS AND CHARACTERIZATION OF 4-IODO-4'-METHYL BENZOPHENONE. Absar A. Faruqui Department of Chemistry, Oregon State University-Corvallis, Oregon 97331

4-iodo-4'-methyl benzophenone was synthesized for the very first time, as no syntheses have been reported in literature. The di-substituted benzophenone was created through Friedel Craft's Acylation. A wide range of characterization was performed including 1D and 2D NMR, IR spectroscopy and GC-MS to prove that molecule is in fact 4-iodo-4'-methyl benzophenone.

PHOTOREDUCTION EFFICIENCY OF 4,4'-DIMETHYLBENZOPHENONE. Susan M. Gino, Department of Chemistry, Oregon State University, Corvallis, OR 97331

4,4'-dimethylbenzophenone was treated with UV radiation for known amounts of time, and the efficiency of photochemical reduction to the corresponding benzpinacol was determined quantitatively. FTIR spectra of the irradiated samples were taken and analyzed to determine this efficiency. Further analysis of the npi* and pipi* regions in the excitation and emission spectra using Grams32 yielded information about these transitions, and this information is displayed in a Jablonski diagram.

17-2004.  Nick Lockhard Comparison of NMR for ketone and corresponding pinacol for 4,4'-dichlorobenzophenone.



Bonn-Savage, Nathan G.
Camp, Elizabeth H.
Donnelly, Michael P.
Faruqui, Absar A.
Gino, Susan M.
Hackim, Abdul
Hasson, Rachelle M.
Herndon, Michael H.
Holcomb, Ryan E.
Huff, Spencer P.
Lindberg, Gerrick E.
Lockhard, Nick
Nishikawa, Rona K.
O Rourke, Luke W.
Sabrowski, Nicholas W.
Simmons, Rashelle A.
Tong, Tony T.