Frank Pickard '05, Becky Shepherd '06, Amber Gillis '06, Meghan Dunn '06, former postdoctoral associate Steve Feldgus, Visiting Professor of Chemistry Karl Kirschner, Winslow Professor of Chemistry George Shields, and two colleagues at Florida State University published an article in the Journal of Physical Chemistry A titled "Ortho-Effect in the Bergman Cyclization: Electronic and Steric Effects in Hydrogen Abstraction by 1-Substituted Naphthalene 5,8-Diradicals."
The researchers present a detailed theoretical study of geometries, electronic structure, and energies of transition states and intermediates completing the full Bergman cycloaromatization pathway of ortho-substituted enediynes with a focus on polar and steric contributions to the kinetics and thermodynamics of hydrogen abstraction. The transformation of these molecules through the Bergman cyclization have potential importance as cancer drugs.
The work was started by Shepherd, Dunn and Gillis the summer prior to their matriculation to college. Gillis and Shepherd pushed the research forward over the next couple of years, and the work was finished by Frank Pickard this past summer and fall. Pickard, a chemical physics major, wrote Hamilton's part of the paper and he is the first author. Pickard is a research assistant in the chemistry department this year, and plans to attend graduate school pursuing computational chemistry. His senior thesis was a study of the Bergman cyclization of the natural product Esperamicin A1, which cleaves DNA and is therefore a potential cancer drug.
Shepherd, the second author on the paper, is a biology major who plans to pursue graduate work in animal behavior/wildlife biology. Gillis, a biochemistry major, is the third author on the paper and plans a career teaching secondary school biology and chemistry. She will attend Union College to pursue a MAT degree. Gillis and Shepherd presented a preliminary version of this research at the 1st MERCURY Conference in Computational Chemistry in July of 2002. Shepherd presented the research twice more as it was progressing, at the 2nd MERCURY Conference in July of 2003 and at the 44th International Symposium on Atomic, Molecular, Biophysical, and Condensed Matter Theory in March of 2004.
Dunn, a chemistry major and fourth author of this work, has applied to graduate school and plans to earn a Ph.D. in environmental chemistry. Tumelano Gopolang '08, also participated in this research this past summer, and presented a poster on the work at the 4th MERCURY conference in July, 2005.
