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Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

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).

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.

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...

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.

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Updated: Jun 2, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Published on: June 10, 2021

1H-Pyrrole-2-carbohydrazide.

Lina Wang¹, Xiangrong Liu, Chun Yang

¹College of Chemistry and Chemical Engineering, Xi'an University of Science & Technology, Xi'an 710054, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|April 28, 2011

Summary

Researchers synthesized a novel compound, C(5)H(7)N(3)O, using ethyl 1H-pyrrol-2-carboxylate and hydrazide hydrate. The crystal structure reveals molecules forming a supramolecular grid through hydrogen bonding.

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

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

Published on: May 21, 2019

Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Ethyl 1H-pyrrol-2-carboxylate is a key organic intermediate.
Hydrazide hydrate is a reactive nitrogen-containing compound.
Hydrogen bonding plays a crucial role in molecular self-assembly.

Purpose of the Study:

To synthesize and characterize a novel compound with the chemical formula C(5)H(7)N(3)O.
To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

Chemical synthesis involving the reaction of ethyl 1H-pyrrol-2-carboxylate and hydrazide hydrate.
Single-crystal X-ray diffraction to determine the molecular and crystal structure.
Analysis of intermolecular interactions, specifically hydrogen bonding.

Main Results:

The title compound, C(5)H(7)N(3)O, was successfully synthesized.
The crystal structure analysis revealed the formation of a supramolecular grid.
Intermolecular N-H⋯N and N-H⋯O hydrogen bonds were identified as the driving force for grid formation.

Conclusions:

The synthesis of C(5)H(7)N(3)O was achieved through a straightforward reaction.
The compound exhibits a well-defined supramolecular structure in the solid state.
Hydrogen bonding is essential for the observed crystal packing and supramolecular architecture.