In this project funded by the Chemical Structure, Dynamics and Mechanisms Program of the Chemistry division, Professor Joel Karty of Elon University will determine the energetic contributions by resonance and inductive effects toward the driving force behind a variety of fundamental organic reactions. The project will incorporate both experimental and computational methodologies. In the experimental methodology, reaction kinetics and thermodynamics will be determined for a variety of reactions involving homologs of the species of interest. The results will then be extrapolated to arrive at the values involving the species of interest. One computational methodology, called a vinylogue extrapolation methodology, incorporates a similar strategy, by utilizing standard molecular orbital theory calculations to determine resonance and inductive contributions toward reactions involving homologs of the species of interest. The second computational methodology is a block-localized wavefunction methodology, the simplest variation of valence bond theory, which allows for the calculations of resonance energies directly. The broader impacts largely surround teaching and training undergraduates in chemistry research, and in the dissemination of that knowledge via publication in major journals, and presentations at professional meetings. Furthermore, the results have the potential to reach broader audiences, such as through their inclusion in undergraduate textbooks, and the development of undergraduate teaching labs.
This work will advance the general understanding of the roles that resonance and inductive effects play throughout chemistry. Moreover, the specific results of this project could have far-reaching impacts on rational drug design, and on the understanding of the role that the amino acid arginine has in the initiation and proliferation of certain types of cancer.
