Tropolone: Difference between revisions

Revision as of 23:51, 9 February 2025

Tropolone

Tropolone is a chemical compound with the molecular formula C_H_O_. It is a member of the class of compounds known as tropones, which are characterized by a seven-membered aromatic ring containing a carbonyl group. Tropolone is notable for its unique structure and properties, which have been the subject of extensive research in organic chemistry.

Structure and Properties

Tropolone is a cyclic ketone with a seven-membered ring, which is unusual compared to the more common six-membered aromatic rings. The presence of the carbonyl group in the ring contributes to its aromaticity, and the compound exhibits tautomerism, existing in equilibrium between keto and enol forms. This tautomeric behavior is depicted in the accompanying diagram.

Synthesis

Tropolone can be synthesized through several methods. One common approach involves the oxidation of cycloheptatriene derivatives. The diagram shows a typical synthetic route starting from cycloheptatriene, which undergoes oxidation to form tropolone. This synthesis highlights the transformation of a non-aromatic precursor into an aromatic compound.

Biological Activity

Tropolone and its derivatives have been studied for their biological activity. They exhibit antimicrobial properties and have been investigated for potential use in pharmaceuticals. The compound's ability to chelate metal ions is also of interest in the development of metal-based drugs.

Related Compounds

Tropolone is structurally related to several other compounds, including:

These compounds share the tropolone core structure and exhibit similar chemical properties.

Related Pages

References

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-'''Tropolone''' is an [[organic compound]] with the [[chemical formula]] C7H6O2. It is a seven-membered [[aromatic]] [[ring]] and is notable for its uncommon 7-membered ring structure. Tropolone was first isolated in 1935 by the German chemist [[Walter Reppe]] and his colleagues, who produced it from [[cresol]] and [[carbon monoxide]] in a process now known as [[Reppe chemistry]].
+== Tropolone ==
-== Structure and properties ==
+[[File:TropoloneGenSynth.png|thumb|right|General synthetic route to tropolone]]
-Tropolone consists of a seven-membered ring with alternating single and double bonds, similar to the structure of [[benzene]]. However, unlike benzene, tropolone has a [[ketone]] functional group at one of its positions. This ketone group is in a state of continuous [[tautomerism]] with a nearby [[hydroxyl]] group, resulting in a structure that is best represented as a [[resonance]] hybrid of two forms.
+[[File:OS_tropolone_from_CpH.svg|thumb|right|Synthesis of tropolone from cycloheptatriene]]
+[[File:TropoloneTaut.svg|thumb|right|Tautomeric forms of tropolone]]
-Tropolone is a pale yellow solid that is soluble in [[water]], [[alcohol]], and [[ether]]. It has a characteristic strong odor and a bitter taste.
+'''Tropolone''' is a [[chemical compound]] with the molecular formula C_H_O_. It is a member of the class of compounds known as [[tropones]], which are characterized by a seven-membered aromatic ring containing a carbonyl group. Tropolone is notable for its unique structure and properties, which have been the subject of extensive research in [[organic chemistry]].
+== Structure and Properties ==
+Tropolone is a [[cyclic ketone]] with a seven-membered ring, which is unusual compared to the more common six-membered aromatic rings. The presence of the carbonyl group in the ring contributes to its aromaticity, and the compound exhibits [[tautomerism]], existing in equilibrium between keto and enol forms. This tautomeric behavior is depicted in the accompanying diagram.
 == Synthesis ==
-Tropolone can be synthesized from [[cresol]] and [[carbon monoxide]] in a process known as [[Reppe chemistry]]. This process involves the [[carbonylation]] of cresol to give a [[lactone]], which is then rearranged to give tropolone.
-== Uses ==
+Tropolone can be synthesized through several methods. One common approach involves the oxidation of [[cycloheptatriene]] derivatives. The diagram shows a typical synthetic route starting from cycloheptatriene, which undergoes oxidation to form tropolone. This synthesis highlights the transformation of a non-aromatic precursor into an aromatic compound.
-Tropolone is used as a [[chelating agent]] in the synthesis of [[metal]] complexes. It is also used as a [[ligand]] in [[organometallic chemistry]]. In addition, tropolone has been studied for its potential use in [[organic electronics]] due to its ability to accept and donate [[electron]]s.
-== Safety ==
+== Biological Activity ==
-Tropolone is considered to be a mild [[irritant]]. It can cause irritation to the [[skin]], [[eyes]], and [[respiratory tract]] if inhaled or contacted.
-== See also ==
+Tropolone and its derivatives have been studied for their biological activity. They exhibit antimicrobial properties and have been investigated for potential use in pharmaceuticals. The compound's ability to chelate metal ions is also of interest in the development of metal-based drugs.
-* [[Hydroxytropolone]]
-* [[Tropolone (data page)]]
+== Related Compounds ==
+Tropolone is structurally related to several other compounds, including:
+* [[Gamma-thujaplicin]]
+* [[Stipitatic acid]]
+* [[Colchicine]]
+These compounds share the tropolone core structure and exhibit similar chemical properties.
+== Related Pages ==
+* [[Tropones]]
+* [[Aromaticity]]
+* [[Tautomerism]]
 == References ==
-<references />
-[[Category:Organic compounds]]
+{{Reflist}}
 [[Category:Ketones]]
-[[Category:Chelating agents]]
+[[Category:Aromatic compounds]]
-[[Category:Ligands]]
+[[Category:Seven-membered rings]]
-[[Category:Organometallic chemistry]]
-[[Category:Organic electronics]]
-{{stub}}