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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...

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.

Structural Isomerism

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly,...

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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Related Experiment Video

Updated: May 1, 2026

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

Remotely triggered geometrical isomerization of a binuclear complex.

Sujoy Karan¹, Thiruvancheril G Gopakumar, Hanne Jacob

¹Institut für Experimentelle und Angewandte Physik, Christian-Albrechts-Universität zu Kiel , 24098 Kiel, Germany.

Journal of the American Chemical Society

|April 16, 2014

Summary

Researchers demonstrated controlled switching in binuclear organometallic molecules. This finding advances understanding of intramolecular electron transfer and spin-coupling in molecular systems.

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

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Published on: July 27, 2022

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Area of Science:

Organometallic chemistry
Molecular electronics
Surface science

Background:

Binuclear organometallic molecules serve as crucial model systems for studying fundamental processes like intramolecular spin-coupling and charge transfer.
Understanding these processes at the molecular level is key to developing advanced electronic devices.

Purpose of the Study:

To investigate intramolecular spin-coupling and charge-transfer processes in binuclear organometallic molecules.
To demonstrate controlled and reversible switching within a single molecular dimer.

Main Methods:

Utilizing electrospray ionization to deposit iron(salen) (Fe(salten)) dimers, linked by dipyridyl disulfide, onto a gold substrate.
Employing low-temperature scanning tunneling microscopy (STM) for atomic-level probing of the molecular structures and their behavior.

Main Results:

Each Fe(salten) monomer within the dimer exhibits multistable behavior due to geometric isomerism.
Demonstrated controlled and reversible remote switching within individual dimers.
Successfully attributed the observed switching mechanism to intramolecular electron transfer.

Conclusions:

Binuclear organometallic molecules can function as multistable switches.
Intramolecular electron transfer is a viable mechanism for controlling molecular switching.
This research provides insights into the design of molecular electronic components.