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2-Piperidinone

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Identification
Molecular formula
C5H9NO
CAS number
675-20-7
IUPAC name
piperidin-2-one;piperidin-3-one;piperidin-4-one
State
State

At room temperature, 2-Piperidinone is typically a liquid, although it can also be found as a crystalline solid if it is cooled below its melting point.

Melting point (Celsius)
38.50
Melting point (Kelvin)
311.70
Boiling point (Celsius)
244.00
Boiling point (Kelvin)
517.00
General information
Molecular weight
99.13g/mol
Molar mass
99.1320g/mol
Density
1.1078g/cm3
Appearence

2-Piperidinone appears as a colorless to pale yellow liquid. It has a distinctive amine-like odor. The compound is hygroscopic, meaning it tends to absorb moisture from the air.

Comment on solubility

Solubility of Piperidinones

Piperidinones, including piperidin-2-one, piperidin-3-one, and piperidin-4-one, exhibit varying solubilities in different solvents. This behavior can be attributed to their molecular structure and the presence of functional groups. Here’s a closer look at their solubility characteristics:

  • Polar Solvents: These compounds tend to be soluble in polar solvents like water and alcohols due to their ability to form hydrogen bonds.
  • Nonpolar Solvents: Conversely, they are less soluble in nonpolar solvents owing to their polar nature.
  • Temperature Effects: Solubility may increase with temperature, which is a crucial factor in practical applications and reactions.

As a general observation, the position of the carbonyl group (C=O) in these compounds influences their solubility profile. For instance, the piperidinone with a carbonyl on the second carbon may show different solubility traits compared to the third or fourth position due to steric factors and electronic effects. In summary, while all three piperidinones share certain solubility traits, the specifics can vary significantly based on their unique structural nuances.

Interesting facts

Interesting Facts about Piperidin-2-one, Piperidin-3-one, and Piperidin-4-one

Piperidinones are a fascinating class of compounds that showcase the versatility of the piperidine ring in organic chemistry. Here are some intriguing details about these specific piperidinones:

Structural Variations

  • Piperidin-2-one: This compound features the carbonyl group positioned at the second carbon of the piperidine ring, making it a prime candidate for different synthetic applications.
  • Piperidin-3-one: Known for its unique structural attributes, this isomer allows for alternative chemical reactivity, showcasing how even a slight shift in structure leads to distinct chemical properties.
  • Piperidin-4-one: With the carbonyl group on the fourth carbon, this variant is particularly interesting for researchers focused on its role in developing various pharmaceuticals.

Applications in Research and Industry

These compounds serve as important building blocks in the synthesis of numerous pharmaceuticals and agrochemicals due to their:

  • Biological Activity: Many piperidinones exhibit significant biological properties, including antibacterial, antifungal, and anticancer activities.
  • Synthetic Versatility: Their unique structures facilitate a variety of reactions, making them useful intermediates in drug development.
  • Potential as Ligands: Some of these compounds can act as ligands in coordination chemistry, broadening their scope in complex formation.

Points of Interest

Aside from their applications, piperidinones also have intriguing characteristics:

  • Strain-Free Rings: The six-membered piperidine ring is strain-free, permitting various functional group modifications, which is crucial for molecular manipulation.
  • Conformational Flexibility: The piperidine ring can adopt different conformations (chair and boat), influencing molecular interactions and reactivity.
  • Historical Significance: The study of piperidine and its derivatives has paved the way for innovations in medicinal chemistry and has been essential in discovering new therapeutic agents.

In conclusion, piperidin-2-one, piperidin-3-one, and piperidin-4-one exemplify the significance of structural diversity in organic compounds, contributing to advancements in various scientific fields. Their impact is visible in everyday applications, making them a crucial topic of study in the realm of chemistry.