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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Isomerism in Alkenes

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...

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Updated: Dec 30, 2025

A Simple Method for the Size Controlled Synthesis of Stable Oligomeric Clusters of Gold Nanoparticles under Ambient Conditions

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Published on: February 5, 2016

Isomerization in Alkynyl-Protected Gold Nanoclusters.

Zong-Jie Guan^1,2, Feng Hu¹, Jiao-Jiao Li¹

¹Department of Chemistry , Tsinghua University , Beijing 100084 , P.R. China.

Journal of the American Chemical Society

|January 21, 2020

Summary

Researchers synthesized two isomeric gold nanoclusters, Au23(C≡CBut)15, revealing isomerism in alkynyl-protected gold nanoclusters for the first time. These isomers display distinct optical properties and unique metal-to-ligand ratios.

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In Situ SIMS and IR Spectroscopy of Well-defined Surfaces Prepared by Soft Landing of Mass-selected Ions

Published on: June 16, 2014

Area of Science:

Inorganic Chemistry
Nanotechnology
Materials Science

Background:

Gold nanoclusters (AuNCs) are promising nanomaterials with tunable properties.
Alkynyl ligands offer unique surface passivation and electronic characteristics for AuNCs.
Understanding isomerism in AuNCs is crucial for controlling their structure-property relationships.

Purpose of the Study:

To report the controlled synthesis and structural characterization of isomeric gold nanoclusters.
To investigate the influence of isomerism on the optical properties of AuNCs.
To explore the electronic structure and potential transformations of these isomeric systems.

Main Methods:

Single-crystal X-ray diffraction for precise structural determination.
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) for composition analysis.
Time-dependent density functional theory (TD-DFT) calculations for electronic structure investigation.

Main Results:

Two isomeric gold nanoclusters, Au23(C≡CBut)15 (Au-1 and Au-2), were successfully synthesized and structurally elucidated.
The metal-to-ligand ratios differ from previously reported AuNC systems.
Isomers exhibit distinct optical properties, with different HOMO-LUMO transition characteristics, and Au-2 can spontaneously transform into Au-1.

Conclusions:

This study presents the first instance of isomerism in alkynyl-protected gold nanoclusters.
The findings provide insights into the synthesis, structure, and isomerism of all-alkynyl-protected gold nanoclusters.
This work encourages further research into isomeric metal nanoclusters and their applications.