Computational studies for the undergraduate laboratory: Identifying site susceptibility to hydroxyl radical attack on aromatic molecules

CHED 112

Phillip Flanders, flanders@jhu.edu1, Mark E. Brandt, brandt@rose-hulman.edu2, Timothy J. Strathmann, strthmnn@uiuc.edu3, and Penney L. Miller, penney.miller@rose-hulman.edu2. (1) Department of Geography and Environmental Engineering, Johns Hopkins University, 3400 North Charles Street, Ames Hall 313, Baltimore, MD 21218, (2) Department of Chemistry, Rose-Hulman Institute of Technology, 5500 Wabash Ave., CM 74, Terre Haute, IN 47803, (3) Department of Civil and Environmental Engineering, University of Illinois at Urbana-Champaign, 205 North Mathews Avenue, Urbana, IL 61801
The improvements in desktop computing and the accessibility of programs such as Spartan allow for greater integration of computational chemistry at the undergraduate level. However, computational methodology has not been widely used to investigate free radical mechanisms in the aqueous phase. Knowing preferred sites for radical attack on organic substrates is highly desirable to elucidate reaction mechanisms. Therefore, we chose hydroxyl radical attack on substituted benzenes (e.g., benzoic acid, nitroanisole, phenol, nitrobenzene) in the aqueous phase as a model system. Our goal was to evaluate how calculated relative energies predicted for the various hydroxyl radical adducts would correspond to product distributions reported in the literature. In order to optimize between accuracy, computational time, and availability of aqueous phase modeling, Hartree-Fock 6-31G* calculations were used (Spartan 06). We are adapting this work to design a laboratory exercise investigating the role of solvation on aqueous radical pathways.
 

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The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008