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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...

Directing and Steric Effects in Disubstituted Benzene Derivatives

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...

Stereoisomers

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...

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,...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Polymer Classification: Stereospecificity

Polymer Classification: Stereospecificity

Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...

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Updated: Jun 14, 2025

Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional π-conjugate Systems

Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional π-conjugate Systems

Published on: February 10, 2020

A guide to bullvalene stereodynamics.

Robert A Ives^1,2, William Maturi^1,2, Matthew T Gill¹

¹Department of Chemistry, University of York Heslington York YO10 5DD UK paul.mcgonigal@york.ac.uk.

Chemical Science

|September 2, 2024

Summary

Bullvalenes exhibit dynamic shapeshifting properties, offering a versatile scaffold for medicinal chemistry. Their unique isomerism provides a rich source of diverse molecular shapes and substituent arrangements for drug discovery.

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Last Updated: Jun 14, 2025

Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional π-conjugate Systems

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Area of Science:

Computational chemistry
Organic chemistry
Medicinal chemistry

Background:

Bullvalenes are fluxional molecules with dynamic valence isomerism.
Conventional ring systems in medicinal chemistry often lack conformational flexibility.
Bioisosteres are crucial for optimizing drug properties by mimicking structural features.

Purpose of the Study:

To analyze the stereodynamic properties of substituted bullvalenes.
To compare bullvalenes with established ring systems used in medicinal chemistry.
To explore bullvalenes as potential bioisosteres in drug discovery.

Main Methods:

Density Functional Theory (DFT) modeling using the 'bullviso' computational tool.
Analysis of principal moments of inertia and exit vector plots.
Classification of rearrangement steps and derivation of an isomer enumeration equation.

Main Results:

DFT-modeled di-, tri-, and tetrasubstituted bullvalenes reveal diverse 3D shapes and exit vectors.
Bullvalenes demonstrate comparable stereodynamic properties to common medicinal chemistry ring systems.
Valence isomerism allows a single bullvalene compound to act as a dynamic covalent library.

Conclusions:

Bullvalenes present a unique scaffold with tunable stereodynamic properties for drug design.
Their shapeshifting nature offers advantages over static ring systems in medicinal chemistry.
Bullvalenes are promising candidates for bioisosteric replacement in drug discovery programs.