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Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.

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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2,4-Dichloro-pyrimidine.

Yan Chen, Zheng Fang, Ping Wei

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study reveals the near-planar structure of a dichlorodinitrogen compound, C4H2Cl2N2. Crystal analysis shows molecules forming chains via intermolecular C-H⋯N interactions.

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Area of Science:

Crystallography
Chemical Physics

Background:

Understanding molecular geometry and intermolecular forces is crucial in chemical structure determination.
Crystal packing influences material properties and reactivity.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C4H2Cl2N2.
To investigate the intermolecular interactions governing crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and non-covalent interactions was performed.

Main Results:

The molecule of C4H2Cl2N2 exhibits a nearly planar geometry, with a maximum atomic deviation of 0.013(3) Å.
Intermolecular C-H⋯N interactions were identified as the primary forces linking molecules into chains within the crystal lattice.

Conclusions:

The crystal structure of C4H2Cl2N2 is characterized by a near-planar molecular conformation.
Intermolecular C-H⋯N interactions play a significant role in the self-assembly of this compound into one-dimensional chains.