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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.

Stability of Substituted Cyclohexanes

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Related Experiment Video

Updated: Jun 2, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Bridge-substituted calix[4]arenes: syntheses, conformations and application.

Conrad Fischer¹, Tobias Gruber, Wilhelm Seichter

¹Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Str. 29, D-09596, Freiberg/Sachsen, Germany.

Organic & Biomolecular Chemistry

|April 21, 2011

Summary

This study details the synthesis and characterization of novel calix[4]arene derivatives. Researchers explored their chemical transformations and conformational properties, revealing insights into their molecular structures.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Last Updated: Jun 2, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Published on: September 18, 2016

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Published on: September 8, 2013

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Crystallography

Background:

Calix[4]arenes are versatile macrocyclic hosts with tunable properties.
Functionalization of calix[4]arenes is key to developing new materials and sensors.
Understanding their conformational behavior is crucial for predicting host-guest interactions.

Purpose of the Study:

To synthesize and characterize novel bridge-substituted calix[4]arene carboxylic acid derivatives.
To investigate the chemical reactivity and conformational properties of these new compounds.
To explore potential applications, such as fluorescent sensing.

Main Methods:

Chemical synthesis of calix[4]arene esters, alcohol, ether, and dansylated derivatives.
Spectroscopic analysis (NMR, fluorescence) for characterization.
Single-crystal X-ray diffraction for solid-state structural determination.
Conformational analysis in solution.

Main Results:

Successfully synthesized a series of calix[4]arene derivatives (esters, alcohol, ether, lactone).
The alcohol derivative showed selective fluorescence quenching by Cu(II) ions.
Unexpected lactone formation was observed during amide synthesis.
X-ray structures revealed an equatorial orientation of the bridge substituent in most compounds.

Conclusions:

The synthesized calix[4]arene derivatives exhibit diverse chemical reactivity.
The conformational preferences of the calix[4]arene scaffold were elucidated.
The fluorescent properties suggest potential for developing metal ion sensors.