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Related Concept Videos

Stereoisomerism02:52

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...
Stereoisomers02:32

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 restricted...
Molecules with Multiple Chiral Centers02:25

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...
Stereoisomerism of Cyclic Compounds02:33

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,...
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

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

Published on: February 15, 2016

Control over stereogenic centres beyond tetracoordination.

Anton Budeev1, Christof Sparr1

  • 1Department of Chemistry, University of Basel St. Johanns-Ring 19 Basel 4056 Switzerland christof.sparr@unibas.ch.

Chemical Science
|February 20, 2026
PubMed
Summary
This summary is machine-generated.

Penta- and hexacoordinate stereogenic centers offer complex stereoisomerism beyond traditional twofold stereogenicity. This review explores their synthesis and applications in diverse fields like medicinal chemistry and catalysis.

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Area of Science:

  • Stereochemistry
  • Main-group and transition metal chemistry

Background:

  • Conventional stereogenic centers are typically tetracoordinate with twofold stereogenicity.
  • Penta- and hexacoordinate stereogenic centers exhibit more complex stereoisomerism, expanding accessible stereochemical space.
  • This complex stereoisomerism is observed in main-group and transition metal compounds with specific ligands.

Purpose of the Study:

  • To summarize the fundamentals of higher-order stereogenicity in penta- and hexacoordinate stereogenic centers.
  • To provide an overview of emerging applications for these complex stereoisomers.
  • To discuss the stereoselective synthesis strategies for compounds with higher-order stereogenic centers.

Main Methods:

  • Literature review focusing on stereochemistry of penta- and hexacoordinate centers.
  • Analysis of stereoisomerism in main-group and transition metal complexes.
  • Exploration of synthetic methodologies for stereoselective synthesis.

Main Results:

  • Penta- and hexacoordinate centers can encode multiple stereoisomers, unlike tetracoordinate centers.
  • This complex stereoisomerism is prevalent in various main-group and transition metal compounds.
  • The field of stereoselective synthesis for these centers is underexplored but holds significant potential.

Conclusions:

  • Higher-order stereogenicity in penta- and hexacoordinate centers offers expanded stereochemical possibilities.
  • These centers have prospective applications in medicinal chemistry, catalysis, and information science.
  • Further exploration of their stereoselective synthesis is warranted to unlock their full potential.