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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).

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...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

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Updated: Jul 7, 2026

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

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

Published on: June 23, 2019

5-Phenyluridine trihydrate.

Thomas Pesnot¹, David L Hughes, Gerd K Wagner

¹School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, England.

Acta Crystallographica. Section C, Crystal Structure Communications

|February 7, 2008

Summary

This summary is machine-generated.

This study details the crystal structure of a novel compound, revealing specific molecular orientations and a unique furanose ring conformation. The molecule forms extensive hydrogen bonds with water molecules, influencing its overall structure.

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Area of Science:

Crystallography
Molecular Biology
Organic Chemistry

Background:

Understanding the three-dimensional structure of nucleoside analogs is crucial for drug design.
The conformation of the ribose sugar moiety significantly impacts nucleoside analog interactions.
Previous studies on synthetic precursors like 5-bromouridine provide a basis for comparison.

Purpose of the Study:

To determine the precise crystal structure of the title compound, C(15)H(16)N(2)O(6).approximately 3H(2)O.
To elucidate the conformational details of the uracil and ribose rings and their relative orientations.
To investigate the intermolecular interactions, particularly hydrogen bonding, within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the compound.
The crystal structure was solved and refined to determine atomic positions and bonding.
Conformational analysis of the furanose ring was performed.

Main Results:

The substituted uracil ring is in the anti position relative to the ribose ring.
The phenyl and uracil rings exhibit a noncoplanar orientation.
The furanose ring adopts a 3'-endo conformation, distinct from the 2'-endo conformation of 5-bromouridine.
An extensive hydrogen-bonding network involving water molecules, some disordered, was observed.

Conclusions:

The determined crystal structure provides detailed insights into the molecular architecture of this nucleoside analog.
The unique 3'-endo furanose conformation may influence biological activity and interactions.
The observed hydrogen-bonding network highlights the role of hydration in stabilizing the crystal structure.