Dr. Thomas Guetzloff


B.S., St. Norbert College, DePere, WI
Ph.D., South Dakota State University

Research Interests

Green Chemistry – Synthesis of N-phenylsuccinimide and N-phenylmaleimide
A microwave-assisted organic synthesis (MAOS) of N-phenylsuccinimide and N-phenylmaleimide are being developed for the second-semester organic teaching laboratory and research purposes. These compounds are in pesticides and these derivatives will be studied at Marshall University.  Utilizing this procedure, N-phenylsuccinimide and N-phenylmaleimides are envisioned to be synthesized by heating in a domestic microwave oven from four to ten minutes in moderate yields (approximately 40%-60%). This technique reduces the reaction time for the traditional synthesis of several hours, which allows the preparation to be achieved in a single organic chemistry laboratory period. This reaction is performed in the absence of solvent; therefore, it represents a ‘greener’ preparation than the traditional synthesis of -phenylsuccinimide and N-phenylmaleimide because it avoids the waste associated with using organic solvents.

Organic Synthesis -Napthalimide Synthesis for on-site detection of metals
Another analytical project of mine is devising a method or protocol that could eventually be designed to provide immediate "on site" testing of the levels of toxic substances (mercury, lead, and cadmium) in aquatic and terrestrial environments using novel fluorescent compounds. Recently a new class of patented naphthalimide compounds have been synthesized that are sensitive to the presence of mercury, lead, and cadmium. It is envisioned that other fluorescent compounds may be synthesized to detect many more heavy metals than just mercury, lead, and cadmium. The new class of fluorescent compounds has a characteristic fluorescent spectrum in the absence of these metals, while in their presence a change in the fluorescence spectra is observed.  Fluorescence is a light emission process that is easily monitored with a fluorimeter, which is a rather inexpensive instrument, compared to EPA standard protocol instruments. The availability of fluorescent detection makes this project very inviting. Since the compounds are sensitive to the presence of the metals a quantitative comparison may be made to determine the amounts of mercury, lead, and cadmium in natural environments. The naphthalimide classes of compounds have a unique chemistry. The compounds could be modified for specific purposes.
We are also looking at the binding studies of these novel dyes with paramagnetic metal ions and other types of metal ions. We are looking at the binding of Na+, Li+, Cu2+, Al3+, Ni2+, Cr3+, Fe3+, Co3+ to the ED4 series of the dye. We are looking for trends in which speciation of individual metals could result.

Soil Chemistry – natural organics interacting with anthropogenic organic material
Another interest is continuing environmental research on organic material (humus) which soil comprises. The percent organic matter in soil and sediment varies greatly, typically ranging from one to ten percent of the total soil composition. Soil organic matter is a very important constituent of soil contributing to factors responsible for: ion exchange capacity, pH buffering capacity, maintenance of soil structure, adsorption of solar energy, immobilization of anthropogenic organic compounds (AOC), metal transport, and water-retention capacity. The organic matter also serves as an energy source or as energy storage for microorganisms, and as nutrients for vegetation. The environmental understanding and importance of soil organic matter interactions with anthropogenic organic compounds is vital to researchers. Creation of more environmental friendly materials and the disposal of toxic materials may be possible with the understanding of soil organic matter. Ultimately the understanding of soil organic matter interactions with anthropogenic organic compounds will help the farmer and researcher to properly use and dispose of pesticides, herbicides, and insecticides on their fields so that these compounds will not contaminate the ground water supply and harm individuals.
I have studied the sorption of atrazine and 2,4-D to humin. I have also looked at the effect of removing different chemical components of the humin. This is done by Soxhlet extracting the humin which removes the lipids, bromination of the humin which removes the remaining organic matter, and by studying whole humin and whole soil. After removal of the components the sorption behavior of atrazine and 2,4-D are measured in an attempt to qualitatively measure each components effect on contaminant sorption.
I will continue to pursue modeling anthropogenic organic compound associations with humus, whole soils, and sediments. These interactions in the past have been attempted by researchers with some success, but there are inherent analytical problems in determining these interactions with a heterogenous material. Research in environmental issues has traditionally been strong for receiving research funds. It is very important to understand the binding interactions of anthropogenic organic compounds with soils as stated above.
Water Quality research – Acid Mine Drainage Water Studies. 
The state of West Virginia is concerned and interested in the water quality of its streams, especially those near existing and abandoned coal mines.  At WVSU we have been fortunate in having the ability to study water issues in our state with the chemistry department's current equipment.  We have been conducting some studies on water quality but have been hampered with the number of samples and analysis of a wide variety of contaminants. The objective of the research is to utilize current atomic adsorption spectrometer (AA) and induced coupled plasma (ICP) to further study the quality of water in an abandoned coal mines with acid mine drainage issues. 

Publications  (* denotes MMC under my supervision)
Guetzloff, T.F.,; Shell, T.; Shell, J.; Poole, K*.; 2009 “Microwave-Assisted Synthesis of N-Phenylsuccinimide” J Chem Educ. 2011 Oct 1;88(10):1439-1441
Rice, J.A; Guetzloff, T.F.; Tombacz, E., 2000, Investigations of Aggregation in Humic Materials Using Scattering Techniques in Humic Substances: Versatile Components of Plants, Soil and Water.  Davies, G.; Ghabbour, E.A. (eds.), Royal Soc. Chem., Cambridge, p. 135-141.
*Farnsworth, T., Jennewein, S., Sorenson, J.C., Guetzloff T.F., Laird, C., “Advances in Ancient DNA Retrieval”.  Proceedings of the South Dakota Academy of Science, 1999, 78:115-127.
*Whiteside, W., *Kurcirek, J., Guetzloff, C.J., Sorenson, J.C., Guetzloff, T.F., “A Study of Herbicide Retention in Two Different Humin Soil Types”. Proceedings of the South Dakota Academy of Science, 1998, 77:47-56.
Guetzloff, T.F., Sorenson, J.C. “Implementation of Multimedia Instruction in Biology and Chemistry Courses: Student Reactions”.  Proceedings of the South Dakota Academy of Science, 1998, 77:73-82.
Xie, H., Guetzloff, T.F., Rice, J.A., “Fractionation of Pesticide Residues Bound to Humin”. Journal of Soil Science, 1997, 162/6: 421-429.
Guetzloff, T.F., Rice, J.A. “Micellar Nature of Humic Colloids” in Humic and Fulvic Acids, Isolation, Structure and Environmental Role.  Gaffney, J.S., Marley, N.A., Clark, S.B., (eds.), ACS Symposium Series 651, American Chemical Society, Washington, DC, 1996, 18-25.
Guetzloff, T.F., Rice, J.A., “Does Humic Acid Form a Micelle”. The Science of the Total Environment, 1994, 152:31-35.
Presentations  (# denotes undergraduate students)
Guetzloff, T.F., Morris B#, Fultz M.  “Synthesis Strategy for A Malemide” American Chemical Society National Meeting, San Diego, Spring 2012.
Abdalla, K.#, Guetzloff, T.F. “Malemide Synthesis” 2nd annual sure Symposium, Summer 2011.  
Guetzloff, T. F., Shell, T. Shell, J.,Davenport, T.#,  Poole, K.#, “Synthesis Strategy for A Malemide” American Chemical Society National Meeting, San Francisco, Spring 2010.
Guetzloff, T. F., Goodall, R.#, Shell, T.,J. Shell, Poole, K.#  Palmer, D.# “Succidimides Synthesis”15th Annual Research Symposium at WVSU, Spring 2009.
Guetzloff, T. F., Shell, T.,  Palmer, D#. “Structural Verification of  Succidimides Synthesis”14th Annual Research Symposium at WVSU, Spring 2008.
Guetzloff, T. F., Shell,  T., Katie Poole# “Synthesis of  Succidimides by novel Techniques”14th Annual Research Symposium at WVSU, Spring 2008.
Guetzloff, T. F., Fletcher, V.,Collette Withkowski# “ Novel Synthesis of ED-4 Compounds” 13th Annual Research Symposium at WVSU, Spring 2007.
Guetzloff, T. F., Fletcher, V., Crystal Gaylor# “Determination of SAMe Metabalites by HPLC” 12th Annual Research Symposium at WVSU, Spring 2006.
Guetzloff, T.F., #Montgomery, N.#, Valentovic., “SAMe Alteration of Acetaminophen Metabolism Detection By HPLC” Annual National American Chemical Society Meeting, Atlanta, Georgia, 2006.
Guetzloff, T.F., #Montgomery, N#., Valentovic, A., "Determination of Reductase in Acetaminophen due to S-Andensoyl-L-methione", NSF REU/SURF 3rdAnnual Undergraduate Research Symposium at Marshall University, Summer 2005.
Dr. Thomas
Dr. Thomas Guetzloff
Analytical Chemistry
Room H223
Phone: (304) 766-4242
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