2003 - 2004 Winners
James Hougas III and Michael Wentzel

James Hougas III

Michael Wentzel

James Hougas's Research Proposal (November, 2003):

     I am currently working on a project with Dr. Mark Freitag.  This research is an Ab Initio (from first principles) study of a reaction that is commonly referred to as the ‘Mannich reaction.’  The Mannich reaction is “…the prototype of carbon-carbon bond forming reactions that involve the addition of resonance-stabilized carbon nucleophiles to iminium salts and imines.”
Dr. Freitag and I are investigating one form of the Mannich reaction that occurs in the liver and has been identified as a possible cause of alcoholic liver damage.  There are currently two proposed mechanisms to the single reaction:

Dr. Freitag and I are attempting to calculate the energetics of each of the possible pathways using standard theoretical techniques.  Upon discovery of the corresponding energies, we will be able to determine which mechanism is most energetically favorable.
Currently, the energetics of the first two steps of path one have been calculated at one level of theory.  This includes the transition states and the calculation of the full pathway connecting reactants to products.

James Hougas's Research Report

Michael Wentzel's Research Proposal (November, 2003):

    We are investigating an alternative to the use of volatile organic compounds(VOCs) in chemical reactions, due to their high costs and harshness.  We propose ionic liquids (fused salts liquid at or below room temperature) as a substitute for VOCs.  Our research hypothesis asked whether ionic liquids could be used as environmentally friendly, recyclable solvents for the formation of amides from carboxylic acids.

Small-scale syntheses are conveniently performed using a direct-coupling of DEET, which is a proven topical mosquito repellent and of current value for control of the West Nile virus transmission.  However, the VOC (CH2Cl2) in this reaction can be replaced by the ionic liquid 1-butly-3-methylimidazolium tetrafluoroborate [(BMIM)BF4]
 Small scale synthesis of DEET in (BMIM)BF4

         Yields for the reaction with (BMIM)BF4 were generally 97-99%.  Currently we are looking for the optimal time, temperature, ionic liquid, and coupling reagent for this reaction.  Analysis is currently being done by HPLC using standard response curves to facilitate the determination of the percent yield of the reaction in (BMIM)BF4.

Michael Wentzel's Research Report