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Nicotine

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Identification
Molecular formula
C10H14N2
CAS number
54-11-5
IUPAC name
1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane
State
State

Nicotine is typically found as a liquid at room temperature. In its purified form, it is a colorless to amber liquid, depending on its exposure to air and contaminants. It is soluble in water and miscible with ethanol and oil.

Melting point (Celsius)
-79.00
Melting point (Kelvin)
194.15
Boiling point (Celsius)
247.00
Boiling point (Kelvin)
520.15
General information
Molecular weight
162.23g/mol
Molar mass
162.2340g/mol
Density
1.0050g/cm3
Appearence

1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane, commonly known as Nicotine, appears as a colorless to pale yellow, oily liquid when in its pure form. It has an acrid, burning taste and a strong, unpleasant odor. However, as it oxidizes, especially when exposed to air, it tends to turn brown due to the formation of nicotine oxide.

Comment on solubility

Solubility of 1,3,3,8,8-Pentamethyl-3-azoniabicyclo[3.2.1]octane

The solubility characteristics of 1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane are quite unique due to its ionic nature. Being a quaternary ammonium compound, it exhibits several noteworthy solubility traits:

  • Highly Soluble in Water: The presence of the quaternary ammonium cation significantly enhances its solubility in polar solvents, particularly water.
  • Limited Solubility in Non-Polar Solvents: Conversely, its solubility in organic solvents tends to be low, as non-polar solvents cannot stabilize the ionic species.
  • Effect of Temperature: The solubility can be affected by temperature; generally, the solubility increases with rising temperature, a common phenomenon in ionic compounds.

This compound demonstrates the general principle that:

"Like dissolves like."

As such, its solubility profile is primarily characterized by strong interactions with water due to its ionic charges, making it more soluble in aqueous environments than in hydrophobic systems. Therefore, a good understanding of the solubility of 1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane is essential for its applications in various fields including synthesis and material science.

Interesting facts

Interesting Facts about 1,3,3,8,8-Pentamethyl-3-azoniabicyclo[3.2.1]octane

1,3,3,8,8-Pentamethyl-3-azoniabicyclo[3.2.1]octane, commonly known in scientific circles for its unique structural properties, represents a fascinating class of compounds known as quaternary ammonium salts. These species exhibit diverse applications in several fields, including organic synthesis and materials science. Here are some interesting aspects to consider:

  • Structure and Stability: The bicyclic structure of 1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane imparts significant steric hindrance, which often contributes to the compound's stability and unique reactivity.
  • Quaternary Ammonium Behavior: As a quaternary ammonium salt, this compound carries a +1 positive charge due to the nitrogen atom's configuration, making it a useful catalyst in various reactions and applications.
  • Application in Synthesis: Compounds such as 1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane play a critical role in organic synthesis, particularly for creating complex molecular architectures.
  • Biological Relevance: The azabicyclo framework is of particular interest in medicinal chemistry, with studies exploring its potential as a pharmaceutical agent, particularly in neurology and cancer research.

As noted by researchers in the field, "The exploration of bicyclic quaternary ammonium compounds opens new horizons in the design of more effective and specialized agents in both synthetic and biological applications."
This compound exemplifies how intricate chemical structures can lead to innovative utility across multiple scientific domains.

Synonyms
1,3,3,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane
1,3,3,8,8-PENTAMETHYL-3-AZABICYCLO[3.2.1]OCTAN-3-IUM
MLS000727748
SMR000306445
cid_13659
SCHEMBL851802
CHEMBL1739798
BDBM80442
AKOS001695074
AKOS022008819
NCGC00245881-01
NCGC00245881-02
AB00614881-07
3,3,5,8,8-pentamethyl-3-azoniabicyclo[3.2.1]octane;iodide