Enolates
When keto-enol tautomerism occurs the keto or enol is deprotonated and an anion, which is called the enolate, is formed as intermediate. Enolates can exist in quantitative amounts in strictly Brønsted acid free conditions, since they are generally very basic. In enolates the anionic charge is delocalized over the oxygen and the carbon . Enolates are somewhat stabilized by this delocalization of the charge over three atoms. In older descriptions of bonding, particularly valence bond theory this was explained by a phenomenon known as resonance.
| Keto-enol-tautomerism | |||||
|---|---|---|---|---|---|
| Interconversion between keto form and enolate; deprotonation of the α-C-atom. | Enolate anion, described is terms of resonance. Left the carbanion. | Interconversion between enolate and enol; protonation of the enolate. | |||
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