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Cyclooctatetraene

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Identification
Molecular formula
C8H8
CAS number
629-20-9
IUPAC name
cyclooctatetraene
State
State

At room temperature, cyclooctatetraene is a liquid.

Melting point (Celsius)
-4.50
Melting point (Kelvin)
268.70
Boiling point (Celsius)
142.50
Boiling point (Kelvin)
415.70
General information
Molecular weight
104.15g/mol
Molar mass
104.1480g/mol
Density
1.0200g/cm3
Appearence

Cyclooctatetraene is a colorless liquid. It has a distinct aromatic odor and is often found in a ring structure due to its unsaturated bonds making it non-planar.

Comment on solubility

Solubility of Cyclooctatetraene

Cyclooctatetraene, with the chemical formula C8H8, exhibits interesting solubility characteristics due to its unique structure and properties. This compound is known for its cyclic arrangement of alternating double bonds, which contributes to its behavior in various solvents.

Regarding solubility:

  • Nonpolar Solvents: Cyclooctatetraene is primarily soluble in nonpolar solvents such as benzene and hexane. This phenomenon occurs because of the similar nonpolar nature of both the solvent and the solute, enhancing solute-solvent interactions.
  • Polar Solvents: In contrast, cyclooctatetraene has very limited solubility in polar solvents like water and alcohols. The significant polarity of these solvents disrupts the nonpolar interactions, leading to poor solvation.

It is worth noting that the solubility of cyclooctatetraene can also be influenced by factors such as:

  1. Temperature: Increased temperatures can enhance solubility in nonpolar solvents.
  2. Concentration: At higher concentrations, the solubility behavior can change due to intermolecular forces becoming more significant.

This compound's solubility pattern underscores the critical role of polarity in solvent-solute interactions, making cyclooctatetraene an intriguing subject for further studies in solubility and chemical behavior.

Interesting facts

Interesting Facts about Cyclooctatetraene

Cyclooctatetraene, often abbreviated as COT, is a fascinating chemical compound that has intrigued chemists for many years. Here are some interesting aspects of cyclooctatetraene:

  • Unique Structure: Cyclooctatetraene is notable for its conjugated diene structure, consisting of eight carbon atoms forming a ring with alternating single and double bonds. This creates a cyclic system that can exhibit significant strain.
  • Planarity vs. Non-planarity: Despite having the potential to be planar, cyclooctatetraene adopts a non-planar "tub" shape. This conformation alleviates angle strain, making it less stable and reactive.
  • Reactivity: COT is known for its remarkable reactivity. It can engage in chemical reactions typical of dienes, especially participating in Diels-Alder reactions. This property makes it a useful precursor in organic synthesis.
  • Antiaromaticity: The compound is an example of a system that is often discussed in terms of aromaticity and antiaromaticity. With eight π electrons, it is classified as antiaromatic, which contributes to its instability.
  • Applications: Cyclooctatetraene has been used in various applications, including in the synthesis of complex organic compounds and as a potential ligand in coordination chemistry.
  • Discovery: The compound was first synthesized in the 1960s, paving the way for further studies on its properties and reactivity, highlighting the advancements in synthetic organic chemistry.

In conclusion, cyclooctatetraene is more than just a simple cyclic hydrocarbon; its structural peculiarities and reactivity profiles offer rich opportunities for scientific exploration and innovation. As chemists continue to study this intriguing compound, its potential applications in various fields may expand even further.

Synonyms
KDUIUFJBNGTBMD-UHFFFAOYSA-N
NS00022580
Q900926