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Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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Related Experiment Video

Updated: Apr 30, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

1-Piperonylpiperazinium picrate.

Channappa N Kavitha¹, Manpreet Kaur¹, Brian J Anderson²

¹Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India.

Acta Crystallographica. Section E, Structure Reports Online

|April 26, 2014

Summary

This study details the crystal structure of a specific salt, revealing how its cation and anion interact through hydrogen bonds and pi-stacking. These interactions influence the molecule's overall crystal packing and network formation.

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Published on: September 26, 2016

Area of Science:

Crystallography
Chemical Physics
Materials Science

Background:

Understanding the precise arrangement of molecules in a crystal lattice is crucial for predicting material properties.
Salts composed of organic cations and anions offer diverse structural possibilities and potential applications.

Purpose of the Study:

To elucidate the detailed crystal structure of the title salt, 4-(2H-1,3-benzodioxol-5-ylmeth-yl)piperazin-1-ium 2,4,6-tri-nitro-phen-o-late.
To analyze the conformational preferences of the cation and anion and their intermolecular interactions within the crystal.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the salt.
Analysis of bond lengths, bond angles, torsion angles, and intermolecular interactions (hydrogen bonds, pi-pi stacking) was performed.

Main Results:

The piperazine ring in the cation adopts a chair conformation, with a specific torsion angle between the piperonyl and piperazine rings.
The nitro groups on the phenolate anion exhibit varying degrees of deviation from the aromatic ring plane.
The crystal structure is stabilized by N-H⋯O hydrogen bonds, C-H⋯O interactions, and centroid-centroid pi-pi stacking between aromatic rings.

Conclusions:

The study provides a detailed structural characterization of the title salt.
The observed intermolecular interactions, including hydrogen bonding and pi-pi stacking, are key determinants of the crystal packing and the formation of a two-dimensional network.