361Phys Chem I Lab
361Phys Chem I Lab
Research interests in my group involve the chemistry of free radicals and radical anions, particularly those that are important to polymeric chemistry and biochemistry. We employ magnetic resonance techniques to explore the chemistry of these systems. My students and I have been very active in looking at the electron initiated cycloaddition of isocyanates that results in the formation of stable isocyanurate anion radicals; both isocyanates and isocyanurates are important in polyurethane chemistry (Organic Letters, 2008, 10, 4521-4524). We are currently exploring the reduction of a variety of aryl substituted isocyanates. My group is also interested in the reactivity between phenoxyl radicals with nitrogen oxide free radicals, both of which are important in many environmental and biological processes. We have just finished investigating the rearrangement mechanism of a stericly hindered nitrocyclohexadienone (2) under anaerobic conditions, see mechanism below (European Journal of Organic Chemistry. 2009, 35, 6104–6108). Notably, we discovered that a key step in this mechanism is the release of the free radical nitric oxide, which is an important biological messenger in numerous living organisms. This reaction is slow enough to observe the transformation of 2 to the final products using our new state-of-the-art Bruker nuclear magnetic resonance spectrometers.
J. B. Morgenthaler, S. J. Peters, D. L. Cedeño, M. H. Constantino, K. A. Edwards, E. M. Kamowski, J. C. Passini, B. E. Butkus, A. M. Young, T. D. Lash and M. A. Jones, “Carbaporphyrin ketals as potential agents for a new photodynamic therapy treatment of leishmaniasis”, Bioorganic & Medicinal Chemistry 2008, 16, 7033-7038.
“Tris-annulenyl Isocyanurate Trianion Triradical and Hexa-anion from the Alkali Metal Reduction of Annulenyl Isocyanate” Peters*, S. J.; Klen, J. R. J. Org. Chem. 2015, 80, 5851-5858.[doi: 10.1021/acs.joc.5b00859]
“Spectroscopic Characterization of 1-Naphthyl Isocyanate Anion Radical and of Tris(1-naphthyl) Isocyanurate Atropisomers” Peters*, S. J.; Kassabaum, M. K.; Nocella, M. K.; McDonald, R. Eur. J. Org. Chem. 2015, 6040-6046.[doi: 10.1002/ejoc.201500863]
“Phenyl Isocyanate Anion Radicals and Their Cyclotrimerization toTriphenyl Isocyanurate Anion Radicals” Servos, M. A.; Smart, N. C.; Kassabaum, M. E.; Scholtens, C. A.; Peters*, S. J. J. Org. Chem. 2013, 78, 3908-3917.[doi: 10.1021/jo4003008]
“The Slow Rearrangement of a Sterically Hindered Nitro-Cyclohexadienone and the Absence of Phenol Oxidation by Nitrogen Monoxide” Peters*, S. J.; Blood, T. M.; Kassabaum, M. E. Eur. J. Org. Chem. 2009, 35, 6104–6108.[doi: 10.1002/ejoc.200901074]