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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).

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Related Experiment Video

Updated: Jun 1, 2026

Multi-photon Intracellular Sodium Imaging Combined with UV-mediated Focal Uncaging of Glutamate in CA1 Pyramidal Neurons

Multi-photon Intracellular Sodium Imaging Combined with UV-mediated Focal Uncaging of Glutamate in CA1 Pyramidal Neurons

Published on: October 8, 2014

2-Amino-pyridinium picrate.

M S Sivaramkumar, R Velmurugan, M Sekar

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This study details the crystal structure of a compound containing cations and picrate anions. Hydrogen bonds link these molecules into a two-dimensional network, revealing specific nitro group orientations.

Area of Science:

Crystallography
Chemical Physics

Background:

The study investigates the molecular arrangement and bonding in a specific chemical compound.
Understanding crystal structures is crucial for predicting material properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(5)H(7)N(2) (+)·C(6)H(2)N(3)O(7) (-).
To analyze the orientation of nitro groups within the picrate anions.
To identify the intermolecular interactions forming the crystal network.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of atomic coordinates and bond lengths/angles.
Identification of hydrogen bonding networks (N-H⋯O and C-H⋯O).

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Multi-photon Intracellular Sodium Imaging Combined with UV-mediated Focal Uncaging of Glutamate in CA1 Pyramidal Neurons

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Main Results:

The asymmetric unit contains two independent cations and anions (A and B).
Nitro groups on the picrate anions exhibit varying degrees of twist relative to the benzene ring.
Intermolecular hydrogen bonds link cations and anions, forming a 2D network.

Conclusions:

The crystal structure reveals specific molecular packing and hydrogen bonding patterns.
The observed nitro group orientations provide insights into intermolecular forces and electronic effects.
The 2D network structure has implications for potential material applications.