What is the Difference Between Pyrrole Pyridine and Piperidine?

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Pyrrole, pyridine, and piperidine are organic compounds containing nitrogen atoms in their chemical structures, and they are known for their basicity. The key difference between these compounds is their basicity, which is as follows:

  1. Pyrrole: Pyrrole is the least basic among the three. It has a five-membered ring structure with a nitrogen atom contributing to the formation of the ring along with four carbon atoms. Pyrrole's basicity is much lower than that of pyridine, with a pKb value of 15.
  2. Pyridine: Pyridine is a moderately basic compound. It has a six-membered ring structure with a nitrogen atom contributing to the formation of the ring along with five carbon atoms. The lone pair of electrons on the nitrogen atom of pyridine is aligned perpendicular, making it more available than that in pyrrole, resulting in higher basicity. Pyridine's basicity is lower than that of piperidine.
  3. Piperidine: Piperidine is the most basic among the three. It has a six-membered ring structure with a fully saturated nitrogen atom contributing to the formation of the ring along with five carbon atoms. Piperidine's basicity is significantly higher than that of pyridine, with a pKb value of 2.8.

In summary, pyrrole is the least basic, piperidine is the most basic, and pyridine has a moderate level of basicity among the three compounds.

Comparative Table: Pyrrole Pyridine vs Piperidine

Pyrrole, pyridine, and piperidine are organic compounds with nitrogen atoms in their chemical structures. They are basic compounds, with pyrrole being the least basic, pyridine being moderately basic, and piperidine being the most basic. Here is a comparison table of their differences:

Property Pyrrole Pyridine Piperidine
Basicity Least basic Moderately basic Most basic
Chemical Formula C4H5N C5H5N (CH2)5NH
Ring Structure 5-membered ring with one nitrogen atom 6-membered ring with one nitrogen atom 6-membered cyclic structure with one nitrogen atom
Boiling Point (°C) 104 125 85.15
Melting Point (°C) -20 -41 -13
Dipole Moment (D) 1.8 1.5 N/A
Applications Pesticides, polar-basic solvent, Karl Fischer reagent in organic synthesis Multiple applications, including pesticides and reagents Pharmaceuticals and other commercial applications

Pyrrole is a volatile and colorless liquid at room temperature, while pyridine and piperidine are solids. The basicity of these compounds is due to the lone pair of electrons on the nitrogen atom, which can be donated to form a bond with a proton.