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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 CNâ ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCNâ...

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...

Coordination Number and Geometry

Coordination Number and Geometry

For transition metal complexes, the coordination number determines the geometry around the central metal ion. Table 1 compares coordination numbers to molecular geometry. The most common structures of the complexes in coordination compounds are octahedral, tetrahedral, and square planar.

[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.

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 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,...

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Published on: June 10, 2021

Coordination isomerism in dioxophosphorane cyanides.

Ayu Afiqah Nasrullah^1,2, Edgar Zander¹, Fabian Dankert³

¹Leibniz Institut für Katalyse e.V. (LIKAT) A.-Einstein-Str. 29a 18059 Rostock Germany christian.hering-junghans@catalysis.de eszter.barath@catalysis.de.

Chemical Science

|March 24, 2025

Summary

The study details alkali metal cyanophosphides and their reactions. Oxidation with oxygen reveals coordination isomerism in dioxophosphoranes, unlike sulfur oxidation.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Published on: February 7, 2019

Area of Science:

Organometallic Chemistry
Main Group Chemistry
Phosphorus Chemistry

Background:

1,3-phosphaazaallenes are thermally labile, forming cyanophosphines.
Deprotonation of cyanophosphines yields cyanophosphides.
Alkali metal cyanophosphides exhibit structural diversity.

Purpose of the Study:

Synthesize and characterize alkali metal tethered cyanophosphides.
Investigate the reactivity of cyanophosphides with oxidants.
Explore coordination isomerism in oxidation products.

Main Methods:

Synthesis of alkali metal cyanophosphides with crown ethers.
Oxidation reactions using O2, S8, and N2O.
X-ray crystallography for structural determination.
Computational studies (DFT) for theoretical insights.

Main Results:

Isolation of alkali metal tethered cyanophosphides [(DippTerPCN)M(crown)].
Formation of dioxophosphoranes [DippTerPO2(CN)]- via oxidation with O2, exhibiting cyanide/isocyanide isomerism.
Synthesis of dithiophosphorane [DippTerPS2(CN)]- without isomerism.
Generation of anionic phoshinidene monoxide adducts using N2O.

Conclusions:

Alkali metal cyanophosphides are versatile synthons.
Triplet oxygen plays a key role in inducing coordination isomerism.
Cyanide isomer is thermodynamically favored over isocyanide.