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Metal-Ligand Bonds

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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,...

Acidity of 1-Alkynes

Acidity of 1-Alkynes

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

Coordination Compounds and Nomenclature

Coordination Compounds and Nomenclature

In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...

Amides to Amines: LiAlH4 Reduction

Amides to Amines: LiAlH₄ Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.

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Updated: May 3, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Unexpected structural motifs in diamine coordination compounds with allyllithium.

Prisca K Eckert¹, Barbara Schnura, Carsten Strohmann

¹TU Dortmund, Anorganische Chemie, Otto-Hahn-Str. 6, 44149 Dortmund, Germany. mail@carsten-strohmann.de.

Chemical Communications (Cambridge, England)

|January 28, 2014

Summary

Researchers synthesized novel diamine coordination compounds using organolithium reagents. One compound uniquely features two distinct organolithium species, explained by quantum chemical calculations.

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Last Updated: May 3, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

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Published on: September 8, 2013

Area of Science:

Organometallic Chemistry
Coordination Chemistry
Computational Chemistry

Background:

Organolithium reagents are crucial in synthetic chemistry.
Diamine ligands are widely used in coordination chemistry.
The synthesis of complexes with multiple, distinct organolithium units remains challenging.

Purpose of the Study:

To synthesize and characterize new diamine coordination compounds.
To investigate the formation of a novel complex containing two different organolithium reagents.
To elucidate the bonding and structural properties using computational methods.

Main Methods:

Synthesis of diamine coordination compounds.
Characterization using spectroscopic techniques (e.g., NMR).
Quantum chemical calculations (e.g., DFT) to study electronic structure and bonding.

Main Results:

Successful synthesis of new diamine coordination compounds with phenyllithium and allyllithium.
Isolation and characterization of a unique complex containing two different simple organolithium reagents.
Computational analysis confirmed the stability and bonding characteristics of the unexpected compound.

Conclusions:

The study presents novel diamine-organolithium complexes.
A groundbreaking diamine complex with two distinct organolithium reagents was achieved.
Quantum chemical calculations provide insight into the formation and structure of this unique coordination compound.