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Concept
Dicarbonyl
Summary
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical (dialdehydes, diketones, diesters, etc.) or unsymmetrical (keto-esters, keto-acids, etc.).
The only 1,2-dialdehyde is glyoxal, . Like many alkyldialdehydes, glyoxal is encountered almost exclusively as its hydrate and oligomers thereof. These derivatives often behave equivalently to the aldehydes since hydration is reversible. Glyoxal condenses readily with amines. Via such reactions, it is a precursor to many heterocycles, e.g. imidazoles.
The principal diketone is diacetyl, also known as 2,3-butanedione, . 1,2-Diketones are often generated by oxidation (dehydrogenation) of the diols:
RCH(OH)CH(OH)R -> RC(O)C(O)R + 2 H2
2,3-Butanedione, 2,3-pentanedione, and 2,3-hexanedione are found in small amounts in various foods. They are used as aroma components in alcohol-free beverages and in baked goods. Benzil, , is the corresponding diphenyl derivative.
A distinctive feature of 1,2-diketones is the long C-C bond linking the carbonyl groups. This bond distance is about 1.54 Å, compared to 1.45 Å for the corresponding bond in 1,3-butadiene. The effect is attributed to repulsion between the partial positive charges of the carbonyl carbon atoms.
1,2-Diketones condense with many bifunctional nucleophiles, such as urea and thiourea to give heterocycles. Condensation with aromatic amines gives diketimine ().
In the cases of 1,2-cyclohexanedione and 1,2-cyclopentanedione, the enol is about 1-3 kcal/mol more stable than the diketo form.
Official source
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