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Nomenclature of Alkynes

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

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.

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.

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...

Anionic Chain-Growth Polymerization: Overview

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...

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Related Experiment Video

Updated: Mar 13, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Published on: February 24, 2015

Pyridyl-Endcapped Polyynes: Stabilized Wire-like Molecules.

Maximilian Krempe¹, Rainer Lippert², Frank Hampel¹

¹Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg (FAU), Germany.

Angewandte Chemie (International Ed. in English)

|October 27, 2016

Summary

Researchers synthesized stable, longer polyynes using a novel pyridyl derivative. These polyynes show potential as molecular wires, linking to metal centers like metalloporphyrins.

Keywords:

electrochemistry ethynyl pyridines molecular wires polyynes porphyrins

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Published on: February 24, 2015

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Area of Science:

Organic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Polyynes are carbon-rich molecules with potential applications as molecular wires.
Previous methods for synthesizing pyridyl-endcapped polyynes were limited in length.
Steric hindrance is a key factor in stabilizing reactive molecular structures.

Purpose of the Study:

To develop a new method for synthesizing longer, stable polyynes.
To explore the utility of these polyynes as linkers in molecular electronics and supramolecular chemistry.

Main Methods:

Synthesis of a 4-ethynylpyridyl derivative with sterically shielding phenyl groups.
Termination of polyyne chains using the synthesized derivative.
Characterization of polyyne stability and length.
Demonstration of coordination to metalloporphyrins.

Main Results:

Successfully synthesized stable polyynes up to the octayne length.
Achieved polyyne lengths twice as long as previously accessible for unstabilized pyridyl-endcapped polyynes.
Demonstrated axial coordination of the pyridyl termini to zinc- and ruthenium-metalloporphyrins.

Conclusions:

The novel pyridyl derivative enables the synthesis of significantly longer and stable polyynes.
These extended polyynes are promising candidates for wire-like linkers in molecular electronic devices.
The coordination chemistry confirms their potential for constructing complex supramolecular architectures.