Structure-Reactivity Behavior of Stabilized Carbanions

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In this project in the Organic Dynamics Program of the Chemistry Division, Professor Claude F. Bernasconi in the Chemistry Department of the University of California, Santa Cruz will study the "Kinetics of Proton Transfer and Nucleophilic Additions to Olefins in Solution and in the Gas Phase". There exist characteristic relationships between the structure of the reactants and the rates at which carbon acids are deprotonated to afford carbanions. This study of how resonance and solvation affect reactivity in carbanion-forming reactions will add to our understanding of chemical reactivity (reaction mechanisms) in general. This project will focus on structure-activity relationships, resonance stabilization and solvation of the carbanion, the solvational state of the base (proton transfers) or the nucleophile (addition reactions) which are particularly pertinent to carbanion-forming reactions. The generality of the suggestion that much of the structure-reactivity behavior of carbanion-forming reactions is governed by a lack of synchronization between bond forming processes and other factors such as resonance development, solvation, intramolecular hydrogen bond formation, steric effects, etc., will be scrutinized and quantified.