RUI: Cycloaromatization of arenediynes

Northern Kentucky University, Newport KY

Investigators

Abstract

The PI's group will first synthesize a number of ten-membered ring enediynes where alkene is part of an aromatic ring or heterocycle. Thermal reaction conditions will then be used to induce Bergman cyclizations of these molecules and the rates and activation energies of these reactions will be measured. The alkene containing components of the endiynes will be varied so that tautomerization, charge dependence, etc (ie electronic effects) on the rates of these reactions can be studied experimentally. The co-PI's group will perform high level calculations to theoretically determine how the electronic character of the ene is related to the experimentally determined rates of these reactions. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. K.C. Russell of the Department of Chemistry at Northern Kentucky University and Dr. Carol A. Parish of the Department of Chemistry at Hobart William Smith College. Drs. Russell and Parish will study a chemical reaction known as the Bergman cyclization. The Bergman cyclization is a chemical reaction which is central to the mechanism of action of a number of anticancer antibiotics. Understanding the electronic effects of changing the structures of the molecules which participates in this type of reaction may one day have revelance in understanding clinical chemistry. Students trained during the course of this work will gain experience in experimental and theoretical and organic chemistry and be aquiring skills needed by the pharmaceutical and speciality chemical industries.