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Stereoisomerism

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

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,...

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

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....

Thermal Sigmatropic Reactions: Overview

Thermal Sigmatropic Reactions: Overview

Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...

Isomerism in Alkenes

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...

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Related Experiment Video

Updated: Jun 14, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Correlated shapeshifting and configurational isomerization.

Burhan A Hussein¹, William Maturi^1,2, Mary Kate Rylands¹

¹Department of Chemistry, Durham University, Lower Mountjoy Stockton Road Durham DH1 3LE UK paul.mcgonigal@york.ac.uk.

Chemical Science

|September 6, 2024

Summary

The constitutional isomerization of bullvalene molecules can be controlled by the configurational isomerization of a carbamate group, enabling correlated motion. This discovery allows for the exploitation of shapeshifting rearrangements in extended molecular structures.

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Last Updated: Jun 14, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Area of Science:

Organic Chemistry
Supramolecular Chemistry
Computational Chemistry

Background:

Bullvalene molecules undergo rapid constitutional isomerization.
Carbamate groups exhibit E-to-Z configurational isomerization.
Controlling molecular rearrangements is crucial for advanced materials.

Purpose of the Study:

To investigate the influence of carbamate configurational isomerization on bullvalene constitutional isomerization.
To elucidate the mechanism of long-range interaction mediating this control.
To explore the potential for exploiting this phenomenon in collective molecular motion.

Main Methods:

Nuclear Magnetic Resonance (NMR) spectroscopy to monitor isomers.
Density Functional Theory (DFT) modeling to understand interactions.
Synthesis of substituted bullvalene with a carbamate group.

Main Results:

The E-carbamate isomer favors the beta-bullvalene form.
The Z-carbamate isomer, via noncovalent interactions, favors the gamma-bullvalene form.
A long-range interaction between the bullvalene core and a pendant phenyl group was identified.

Conclusions:

Carbamate configurational isomerization can remotely control bullvalene constitutional isomerization.
Noncovalent interactions play a key role in mediating this long-range effect.
This controlled shapeshifting can be utilized for collective motion in extended molecular systems.