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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

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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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2-Amino-pyrimidinium picrate.

B Narayana, B K Sarojini, K Prakash Kamath

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details the crystal structure of a compound, revealing typical geometric parameters. Molecular arrangements show specific nitro group orientations and hydrogen bonding interactions within crystal planes.

Area of Science:

Crystallography
Chemical Physics

Background:

Understanding molecular geometry and intermolecular forces is crucial in chemical physics.
Picrate salts are common subjects of structural analysis due to their properties.

Purpose of the Study:

To determine the precise geometric parameters of the title compound, C(4)H(6)N(3) (+)·C(6)H(2)N(3)O(7) (-).
To investigate the spatial arrangement of nitro groups and hydrogen bonding within the crystal structure.

Main Methods:

X-ray crystallography was employed to analyze the crystal structure.
Geometric parameters, including dihedral angles and hydrogen bond distances, were measured.

Main Results:

The compound exhibits typical geometric parameters within expected ranges.

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Two nitro groups are nearly coplanar with the picrate ring (dihedral angles ~3-4°), while the third is significantly twisted (dihedral angle ~46°).

N-H⋯O hydrogen bonds link cations and anions, with molecules crystallizing in planes parallel to (11).

Conclusions:

The crystal structure reveals specific conformational preferences of the nitro groups.
Intermolecular hydrogen bonding plays a significant role in the compound's solid-state organization.