The objective of this research is to evaluate the resonance stabilization carbonyls and imines impart to alkenes. The resonance stabilization of a carbon-carbon double bond conjugated to the carbon-oxygen double bond (C=O) of aldehydes is widely accepted. However, the focus is primarily on the carbonyl's stability rather than on the carbon-carbon double bond. Reports of the resonance stabilization energies of enimines have been considerably less numerous. While conjugated enimines (C=C-C=N) have been used synthetically for decades, there has been little investigation into the resonance stabilization of these compounds.  The determination of resonance stabilization will be accomplished by measuring the heat of hydrogenation for conjugated compounds and comparing it to that of non-conjugated compounds.   The heats of hydrogenation will be determined for a series of conjugated ketones and aldehydes and corresponding enimines with varying structures to probe the effect structure has on resonance stabilization and therefore on the extent of conjugation.

Studies on the resonance stabilization of conjugated aldehydes and corresponding imines

243rd National Meeting (2012)

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