Resonance effects and inductive effects are staple concepts in undergraduate organic chemistry, invoked routinely to explain a wide variety of chemical phenomena. But when we invoke these concepts, we typically do so qualitatively, not quantitatively. This is not surprising when we consider the fact that resonance and inductive effects are often present simultanously within a molecular species, and separating the effects was made possible only within the last few decades with the advances in computational chemistry and computing power. Over the last 15 years, my research group has exploited these advances, developing a vinyloge extrapolation methodology that allows us to quantify the two effects separately. We have applied the methodology to numerous fundamental organic systems, including functional group acidities, S<sub>N</sub>2 energy barriers, and Y-aromaticity. This talk will explore the lessons we have learned from these studies. Some of the lessons are ones that move us toward a more complete understanding of resonance effects and inductive effects in general. Other lessons are ones that pertain to the benefits that students gain from conducting this kind of research.

Lesson learned about resonance effects and inductive effects: Application of a vinylogue methodology toward fundamental organic systems

254th National Meeting (2017)

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