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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.

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.

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.

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

α-Alkylation of Ketones via Enolate Ions

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...

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.

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Updated: Jan 8, 2026

Author Spotlight: Accelerating Discovery in Microporous Material Chemistry

Author Spotlight: Accelerating Discovery in Microporous Material Chemistry

Published on: October 6, 2023

Unveiling the alkyne-π interaction using metal-organic cage compounds.

Junrui Liu^1,2,3, Shujun Ning¹, Ting Chen^1,2,3

¹CAS Key Laboratory of Design and Assembly of Functional Nanostructures, Fujian Provincial Key Laboratory of Nanomaterials, and State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian, China.

Communications Chemistry

|December 12, 2025

Summary

Researchers discovered the alkyne-π interaction, a crucial intermolecular force in chemistry and biology. This interaction influences spectroscopic properties and has implications for designing new functional materials and improving bio-imaging resolution.

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Synthesis and Characterization of Functionalized Metal-organic Frameworks

Synthesis and Characterization of Functionalized Metal-organic Frameworks

Published on: September 5, 2014

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Last Updated: Jan 8, 2026

Author Spotlight: Accelerating Discovery in Microporous Material Chemistry

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Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

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Published on: May 12, 2023

Synthesis and Characterization of Functionalized Metal-organic Frameworks

Synthesis and Characterization of Functionalized Metal-organic Frameworks

Published on: September 5, 2014

Area of Science:

Supramolecular Chemistry
Materials Science
Chemical Physics

Background:

Alkynes are vital in synthesis, bio-imaging, and drug design.
Intermolecular interactions involving alkynes remain largely unexplored.
Understanding these interactions is key to rationalizing material properties.

Purpose of the Study:

To identify and characterize the alkyne-π interaction.
To investigate the influence of alkyne-π interactions on spectroscopic properties.
To explore the potential applications of alkyne-π interactions in functional materials.

Main Methods:

Comparison of two zirconocene metal-organic cage compounds.
Analysis of single-crystal structures and C≡C vibrational signals.
Computational studies and Cambridge Crystallographic Data Centre (CCDC) database survey.

Main Results:

The alkyne-π interaction was confirmed as a genuine intermolecular interaction.
Alkyne-π interactions significantly impact spectroscopic properties, despite lower energy compared to π-π interactions.
The interaction is prevalent in hundreds of crystal structures.

Conclusions:

Alkyne-π interactions are a fundamental force influencing molecular properties.
These interactions offer strategies for enhancing bio-imaging resolution.
They serve as a signature for designing alkyne-containing supramolecular structures and functional materials.