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The keto and enol tautomers of acetylacetone coexist in solution. The enol form has C 2v symmetry, meaning the hydrogen atom is shared equally between the two oxygen atoms. [4] In the gas phase, the equilibrium constant, K keto→enol, is 11.7, favoring the enol form.
Some examples of tautomers Keto-enol tautomerization typically strongly favors the keto tautomer, but an important exception is the case of 1,3-diketones such as acetylacetone. [ 6 ] Tautomerization is pervasive in organic chemistry .
Keto–enol tautomerism refers to a chemical equilibrium between a "keto" form (a carbonyl, named for the common ketone case) and an enol. The interconversion of the two forms involves the transfer of an alpha hydrogen atom and the reorganisation of bonding electrons .
Tautomers of a substituted HNacNac ligand precursor and an idealized complex (right) of the conjugate base (M = metal, L = other ligand) NacNac is a class of anionic bidentate ligands. 1,3-Diketimines are often referred to as "HNacNac", a modification of the abbreviation Hacac used for 1,3-diketones. These species can exist as a mixture of ...
Ethyl acetoacetate is subject to keto-enol tautomerism. In the neat liquid at 33 °C, the enol consists of 15% of the total. [5] The enol is moderately acidic. Thus ethyl acetoacetate behaves similarly to acetylacetone: [6] CH 3 C(O)CH 2 CO 2 C 2 H 5 + NaH → CH 3 C(O)CHNaCO 2 C 2 H 5 + H 2. The resulting carbanion undergoes nucleophilic ...
Keto-enol tautomerism. 1 is the keto form; 2 is the enol. Ketones that have at least one alpha-hydrogen, undergo keto-enol tautomerization; the tautomer is an enol. Tautomerization is catalyzed by both acids and bases. Usually, the keto form is more stable than the enol. This equilibrium allows ketones to be prepared via the hydration of alkynes.
Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion (CH 3 COCHCOCH − 3) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring.
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