Experimental Chemistry II, CH 463 & 463H Poster Abstracts for 2005

Department of Chemistry – Oregon State University

June 2, 2005   1:30 – 3:30

Gilbert Addition 313
Alphabetical List of Authors


1-2005. SYNTHESIS AND CHARACTERIZATION OF 4-BROMO-4'-METHOXYBENZOPHENONE.  Tyler E. Serrill, Department of Chemistry, Oregon State University, Corvallis, OR 97331


The synthesis was carried out via a Friedel-Crafts acylation.  The product was then characterized through the use of TLC, H NMR, FT-IR, and melting point determination.  Through these various techniques the identity of the product was confirmed to be 4-bromo-4'-methoxybenzophenone.


 2-2005.  PHOTOTREDUCTION OF 4-CHLORO-4'-METHYLBENZOPHENONE. Amber J.Taylor, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331


The ability of 4-chloro-4'-methylbenzophenone to form the benzopinacol has been widely documented. In this study, the quantum efficiency of this reaction was determined to be 0.5224.



3-2005.  SYNTHESIS AND CHARACTERIZATION OF 4-BROMO-4'-METHYLBENZOPHENONE.  Jesse J. Allen, Department of Chemistry, Oregon State University, 97332


An experimental synthesis for the benzophenone of interest was developed and successfully carried through utilizing a Friedel-Crafts acylation.  The product was then characterized using various spectroscopic techniques.



4-2005.  SYNTHESIS AND CHARACTERIZATION OF 4-CHLORO-4'-METHOXYBENZOPHENONE.  B.L. James, Department of Chemistry, Oregon State University, Corvallis, OR 97332


4-chloro-4’-methoxybenzophenone was synthesized via the Friedel-Crafts method with anisole and 4-chlorobenzoyl chloride.  It was recovered with a 64% yield after recrystallization in isopropyl alcohol.  The product was characterization through NMR, IR, and melting point.  These techniques provided sufficient data to conclude that the product was both pure and the benzophenone desired.





Individual substituted benzophenone synthesis was performed to produce 4,4’-dimethylbenzophenone (4,4’-DMBP) via Friedel-Crafts acylation.  Specific solvents and reagents, respectively, included toluene in nitrobenzene, toluoyl chloride as the acyl chloride and aluminum chloride as the catalyst. Characterization included determining melting point, Infrared analysis and Nuclear Magnetic Resonance leading to a yield of 73%. Using ethanol as a polar solvent and methyl cyclohexane as a non-polar solvent, data acquisition was then performed and phosphorescence analyses of the

npi* and pipi* transitions were then executed.  These analyses showed a shorter wavelength in the polar solvent, therefore indicating a blue shift.



6-2005.  PHOTOPHYSICAL PROPERTIES OF 4-CHLOROBENZOPHENONE IN POLAR AND NON-POLAR SOLVENTS.   D.R Valencia, Department of Chemistry, Oregon State University, Corvallis, OR 97330.


Through UV spectroscopy, photophysical and photochemical properties
were determined for 4-chlorobenzophenone. Transition and vibrational states
were analyzed in two separate polar and non-polar solutions, ethanol
and menthylcyclohexane. The product was exicted and characteristics of the
triplet state were analyzed. UV spectra of the n-pi and pi-pi*
transitions and all photophysical parameters are presented.


7-2005.  AN NMR STUDY OF 4-METHOXY-4'-METHYLBENZOPHENONE AND AN UKNOWN DISTILLATE . Erika G. Condos, Department of Chemistry, Oregon State University.


The following characterizations for 4-methoxy-4-methylbenzophenone and an unknown that distilled at 212oC in a 3 torr vacuum, such as H NMR, 13C NMR, HSQC and HMBC, were used to distinguish the two products.  The charts will show that 4-methoxy-4’-methylbenzophenone, a pale green product, was indeed synthesized and purified via vacuum distillation.  A pink product, which is currently unknown, is suspected to be a result of overheating/burning the unpurified mixture during the initial vacuum distillation.  It is my intention to determine what the product is once these tests are obtained.


8-2005.  ELECTRONIC TRANSITIONS AND HOW THEY’RE AFFECTED BY THE SOLVENT’S POLARITY. R.L. McElroy, Department of Chemistry, Oregon State University-Corvallis, OR 97331


The electronic transitions of 4-bromo-4’-fluorobenzophenone were investigated in a polar and nonpolar solvent.  Using a polar solvent, ethanol, the npi* transition was blue shifted to 324.5 nm with respect to 344.7 nm for methylcyclohexane.  The pipi* transitions, however, didn’t exhibit a red shift, which you would expect. Models of this compounds orbitals were explored as a way to explain this characterization. 



9-2005.   SYNTHESIS AND DOUBLE SOLVENT STUDY ON 4-BROMO-4'-PROPYLBENZOPHENONE; S.H. Porter; Department of Chemistry, Oregon State University, Corvallis, Oregon 97331


Using the Friedel Crafts method, 4-bromo-4’-benzophenone (BPBP) was synthesized from n-propylbenzene and 4-bromobenzoyl chloride. It was found to have a melting point of 91°C at 760 mmHg and a boiling point of 204°C under 6 mmHg. FT-IR, NMR and absoption spectrum for both solvents were done on the BPBP. From the spectra a Jabloniski diagram was constructed.  


10-2005.  HNMR AND IR CHARACTERISTICS OF 4-4'-DIMETHOXYBENZOPHENONE COMPARED WITH THE PHOTOREDUCED BENZPINACOL. Christopher L. Koyama, Department of Chemistry, Oregon State University, Oregon 97331


The photoreduction of 4-4'-dimethoxybenzophenone (DMBP) into a benzpinacol doubles the integration values for the proton peaks due to symmetry. A broad -OH peak around 3 ppm displays the benzpincaol characteristic. The IR spectrum has an increase in the amount of aromatic C-H stretches combined with the loss of the carbonyl, and the addition of an alcohol band at 3550/cm completes the photoreduction spectra. 


11-2005.  SHIFTS IN THE PHOTOCHEMICAL PROPERTIES DUE TO POLARITY OF SOLVENTS; Raymond F. Carl; Undergraduate in chemistry at Oregon State University Corvallis Oregon 97331


The effect of the polarity on the UV emission and excitation of
4,4’-difluorobenzophenone was explored using a polar solvent, Ethanol (EtOH), and a non-polar solvent, methyl cyclohexane (MCH).  It was observed that the npi* transitions were shifted to shorter wavelengths a hypsochromic or blue shift in the polar solvent.  The shift is due to the solvation of the non-bonding electrons which lowers the energy of the n orbital.


12-2005.   4-CHLORO-4'-PROPYL-BENZOPHENONE PHOTOCHEMISTRY AND PINNACOL FORMATION. Rebecca E. Schutz, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331.


Following the successful synthesis of 4-chloro-4'-propyl-benzophenone, a quantitative photochemistry study was performed using ultraviolet radiation.  When making solutions for analysis, some amount of estimation was involved due to the lack of published information on the product.  Also, an assumption was made, that as the ketone disappeared, the pinnacol was formed at the same rate.  Standard dilutions of the product in IPA and a stock solution, made at 0.0502 M, were used for comparisons in the disappearance of the ketone, over set times.  Using three of the four times studied, due to a contaminant in one sample, the pinnacol was formed with a photoreduction quantum efficiency of 179%.


13-2005.  SOLVENT STUDY of 4,4’-DIBROMOBENZOPHENONE in ETHANOL and METHYLCYCLOHEXANE. Jonathan E. VanDyke 2620 S.W Wester Blvd #305 97333


The interactions of 4,4’-dibromobenzophenone in ethanol and methylcyclohexane were studied. UV spectroscopy and phosphoresces was used to identify differences in the transition states witnessed between two solvents, polar ethanol and non-polar methylcyclohexane. A non-polar to polar n-pi* blue shift (348nm to 334nm) and a pipi* red shift (443nm-446nm) were observed. This when compared to literature values (2) yield the expected trend.


14-2005.  SYNTHESIS AND OTHER INTERESTING FACTS OF P-AMINOBENZOPHENONE David B Chan Department of Chemistry Corvallis, OR 97331


A unique synthesis of p-aminobenzophenone from aniline and benzoic acid using polyphosphoric acid as the Lewis acid catalyst for Friedel-Crafts acylation. Purification was done via silica gel flash chromatography and recrystallization in hot aqueous ethanol.  Also the charge transfer-like characteristic caused by the free lone pair on the amine substituent gives rise to two triplet states; T1 n-pi* and T2 pi-pi*.


 15-2005.  QUANTITATIVE AND QUALITATIVE DETERMINATION OF 1,2-DIPHENYL-1,2-DITOLYLETHANEDIOL.  J.A. Klein, Dept. of Chemistry, Oregon State University, Corvallis, 97330


The quantum efficiency of photoreduction (phi red ) for 4-methylbenzophenone to the benzopinacol, 1,2-Diphenyl-1,2-ditolylethanediol has been determined to be 0.448. It is also expected that benzopinacol was formed qualitatively over the course of three weeks in a photoreactor (350 nm) but conclusive results that the pinacol was formed were not obtained via NMR or melting point.  However, FTIR data indicates that the pinacol was formed.




Abstract: The quantum efficiency of the UV photoreduction of 4-fluorobenzophenone to the associated benzopinacol is measured via quantitative IR spectroscopy of the carbonyl region not obscured by extensive solvent IR absorption.


17-2005. SUBSTITUENT EFFECTS OF HALOGENATION AT THE 4,4’ POSITIONS OF BENZOPHENONE IN THE INFRARED. J.A. Tengwall. Department of Chemistry. Oregon State University. Corvallis, Oregon, 97333.


Benzophenone and its derivatives have found their use as a popular additive to a variety of materials where damage from UV radiation is of concern. Hence, a better understanding of substituent effects on the benzophenone system is necessary. This study aims to reveal the extent by which halogenation of benzophenone at the 4,4’ positions will split and/or shift the absorption frequencies of the normal modes of vibration.


18-2005. COMPARISON OF TRANSITION STATES FOR 4-FLUORO-4’-METHOXYBENZOPHENONE USING A POLAR AND NON-POLAR SOLVENT STUDY. Jessica McElravy, Department of Chemistry, Oregon State University, Corvallis, Oregon, 97331.


Using UV absorption spectroscopy and phosphorescence, the transition states pipi* and npi* for 4-fluoro-4’methoxybenzophenone were analyzed and compared using a polar solvent, Ethanol, and a non-polar solvent, Methylcyclohexane.  It was determined using this data that the polar solvent interacted with the 4-fluoro-4’-methoxybenophenone leading to a charge transfer from the extra lone pairs found in the methoxy substituent eliminating an observed npi* transition.  Also, using the polar solvent led to a red shift, lower pi* energy, in the pipi* transition. The vibrations found in each transition state were observed and analyzed to find that in the pipi* transitions, two vibration transitions were occurring in this molecule.  The first is the C-H Stretch and the second a C-H bend.  The npi* transition also showed signs of the C-H bend instead of the expected C=O stretch.  This provided information on what was occurring structurally during each transition state for this molecule.


19-2005.  SYNTHESIS, CHARACTERIZATION, AND PHOTOCHEMISTRY OF 4,4'-DICHLOROBENZOPHENONE. Sulistiono Herlambang, Department of Chemistry, Oregon State University, Corvallis, Oregon 97331.


A well–known of 4,4’–dichlorobenzophenone with the melting point of 145.6°C ± 0.4°C was synthesized using the Friedel–Crafts Acylation from 4–chlorobenzoyl chloride and aluminum chloride in chlorobenzene as a solvent. To ensure the desired pure products were made, the 1H–NMR, 13C–NMR and IR data of the product were achieved. Furthermore, the Jablonski diagram for n–π* transition and π–π* transition revealing the molecular vibrations was generated from the study of the pure 4,4’–dichlorobenzophenone in ethanol solvent at room temperature and 77 K spectrophotochemistry.


20-2005.  POLAR VS. NON-POLAR:  SOLVENT EFFECTS ON THE PHOTOPHYSICS/PHOTOCHEMISTRY OF 4,4' DIMETHOXYBENZOPHENONE.  T.J. Brunscheon, Department of Chemistry, Oregon State University, Oregon, 97330


The effects of solvent polarity on the photophysics/photochemistry of the 4,4' dimethoxybenzophonone molecule will be explored.  Special attention being paid to the effects noted in low temperature studies, exploring the reasoning behind differing electronic transition data.



Jordan K. Boutilier boutilij@onid.orst.edu

4-bromobenzophenone was synthesized from bromobenzene and benzoyl chloride in the presence of an aluminum chloride catalyst. The final product was subjected to a series of physical studies designed to characterize the compound and study its photophysical parameters.


List of Authors:
Allen, Jesse, J.

Boutilier, Jordan K.

Braucht, Jennifer L.

Brunscheon, Tristan J.

Carl, Raymond F.

Chan, David

Condos, Erika G.

Herlambang, Sulistiono

James, Brandon L.

Klein, Joel A.

Koyama, Christopher L.

Mc Elravy, Jessica K.

Mc Elroy, Rebecca L.

Porter, Spencer H.

Schutz, Rebecca E.

Serrill, Ty E.

Starr, Nathan G.

Taylor, Amber J.

Tengwall, Jeffrey A.

Valencia, Darlene R.

Van Dyke, Jonathan E.


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