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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...

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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Updated: Dec 8, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

4,15-Dimethyl-7,12-diazo-niatri-cyclo-[10.4.0.0^2,7]hexa-deca-1(12),2,4,6,13,15-hexa-ene dibromide monohydrate.

Edward J Behrman¹, Alexandar L Hansen², Chunhua Yuan²

¹Department of Chemistry & Biochemistry, The Ohio State University, 484 W. 12th Avenue, Columbus, Ohio, 43210, USA.

Acta Crystallographica. Section E, Crystallographic Communications

|September 17, 2020

Summary

This study details a new viologen compound, a type of redox indicator. Researchers present its synthesis, crystal structure, and NMR spectral analysis.

Keywords:

atropisomer crystal structure synthesis viologen

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Published on: September 18, 2016

Area of Science:

Organic Chemistry
Crystallography
Electrochemistry

Background:

Viologens are quaternary salts of di-pyridyls.
They are valuable as redox indicators due to their significant negative one-electron reduction potentials.

Purpose of the Study:

To present the crystal structure of a specific viologen compound (1).
To detail an improved synthesis method for compound (1).
To provide a comprehensive analysis of its NMR spectra.

Main Methods:

X-ray crystallography was used to determine the crystal structure.
An improved synthetic route was developed.
Nuclear Magnetic Resonance (NMR) spectroscopy was employed for spectral analysis.

Main Results:

The crystal structure of compound (1), C16H20N2 2+·2Br-·H2O, was elucidated.
A novel synthesis for this viologen was successfully developed.
Detailed NMR spectral data were obtained and analyzed.

Conclusions:

The study successfully characterized a new viologen compound.
The findings contribute to the understanding of viologen structures and synthesis.
The presented data are valuable for applications in redox indication and materials science.