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Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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...

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...

Complexation Equilibria: The Chelate Effect

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...

Chirality in Nature

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

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Related Experiment Video

Updated: Nov 11, 2025

Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

Published on: August 31, 2018

Chiral Gold(III) Complexes: Synthesis, Structure, and Potential Applications.

Rémi Jouhannet¹, Samuel Dagorne¹, Aurélien Blanc²

¹Equipe de Synthèse, Réactivité et Catalyse Organométalliques, UMR 7177 CNRS), Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081, Strasbourg, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|March 29, 2021

Summary

Chiral gold(III) complexes offer enhanced control for synthesizing complex organic molecules, overcoming limitations of gold(I) catalysts. Their unique geometry also shows promise in pharmaceutical applications.

Keywords:

catalysis chiral ligands enantioselectivity gold

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Related Experiment Videos

Last Updated: Nov 11, 2025

Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

Published on: August 31, 2018

Synthesis of Near-Infrared Emitting Gold Nanoclusters for Biological Applications

Synthesis of Near-Infrared Emitting Gold Nanoclusters for Biological Applications

Published on: March 22, 2020

Synthesis and Characterization of Amphiphilic Gold Nanoparticles

Synthesis and Characterization of Amphiphilic Gold Nanoparticles

Published on: July 2, 2019

Area of Science:

Organometallic Chemistry
Catalysis
Medicinal Chemistry

Background:

Homogeneous gold catalysis has become vital for synthesizing complex organic scaffolds since the 2000s.
Achieving enantioselective transformations with gold catalysts is challenging due to the linear geometry of gold(I) complexes.

Purpose of the Study:

To explore the synthesis and applications of chiral gold(III) complexes.
To address the limitations of gold(I) in enantioselective catalysis.
To highlight the potential of gold(III) complexes in catalysis and pharmacology.

Main Methods:

Review of syntheses of well-defined gold(III) complexes.
Summary of applications in catalysis and pharmacology over the last 15 years.

Main Results:

Gold(III) complexes, with their square planar geometry, are more suitable for chiral induction compared to gold(I).
Gold(III) complexes demonstrate significant potential in both catalytic and pharmacological fields.

Conclusions:

Chiral gold(III) complexes represent a promising area for advancing enantioselective synthesis.
The unique properties of gold(III) complexes warrant further investigation for catalytic and therapeutic applications.