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Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Chair Conformation of Cyclohexane

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...

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.

Naming Enantiomers

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

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Updated: Jun 15, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Sequence isomerism in [3]rotaxanes.

Anne-Marie L Fuller¹, David A Leigh, Paul J Lusby

¹School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ United Kingdom.

Journal of the American Chemical Society

|March 17, 2010

Summary

This summary is machine-generated.

Researchers developed a new method to precisely sequence macrocycles on rotaxane threads. This technique creates distinct stereoisomers by mechanically locking the macrocycle order, enabling controlled molecular assembly.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Materials Science

Background:

Precise sequential assembly of molecular components is crucial for creating complex functional architectures.
Rotaxanes, interlocked molecular structures, offer unique possibilities for mechanical control and information storage.
Controlling the sequence of multiple macrocycles on a single molecular thread remains a synthetic challenge.

Purpose of the Study:

To develop a general strategy for the sequential and controlled assembly of different macrocycles onto a nonsymmetrical rotaxane thread.
To demonstrate the synthesis of [3]rotaxane diastereomers with mechanically dictated macrocycle sequences.
To explore the potential for creating complex, multi-ring rotaxanes with predetermined structural arrangements.

Main Methods:

Iterative coordination of palladium(II) pyridine-2,6-dicarboxamide complexes to a pyridine ligand on a rotaxane thread.
Macrocyclization via ring-closing olefin metathesis to secure each macrocycle.
Sequential removal of palladium(II) templates to allow for subsequent complexation and macrocyclization, ensuring precise sequencing.

Main Results:

Successful synthesis of a pair of [3]rotaxane diastereomers that differ only in the sequence of their macrocycles.
Demonstration of mechanical control over macrocycle arrangement, leading to stereoisomerism analogous to atropisomerism.
Establishment of a method for building multiring rotaxanes with a predetermined sequence of macrocycles.

Conclusions:

The described strategy provides precise sequential control over macrocycle assembly on rotaxane threads.
This method enables the synthesis of complex rotaxane architectures with mechanically enforced stereochemistry.
The findings open avenues for designing sophisticated molecular machines and materials with tailored properties.