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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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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.
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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

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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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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Synthesis and Characterization of Amphiphilic Gold Nanoparticles
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A Gold(I)-Acetylene Complex Synthesised using Single-Crystal Reactivity.

Chloe L Johnson1, Daniel J Storm2, M Arif Sajjad2

  • 1Department of Chemistry, University of York, York, YO10 5DD, UK.

Angewandte Chemie (International Ed. in English)
|May 3, 2024
PubMed
Summary

Researchers synthesized a novel gold(I) acetylene complex using single-crystal to single-crystal solid/gas reactions. This study details the structure and bonding of this unique gold-alkyne compound.

Keywords:
X-ray diffractionacetylenebulky phosphinegold(I)ligand cavitysingle crystalssolid-state organometallic

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Area of Science:

  • Organometallic Chemistry
  • Solid-State Chemistry

Background:

  • Gold(I) complexes are valuable catalysts and synthetic intermediates.
  • Understanding alkyne coordination to gold is crucial for catalysis and materials science.

Purpose of the Study:

  • To synthesize and characterize the simplest gold(I) acetylene complex.
  • To investigate the solid/gas reactivity of gold(I) carbonyl complexes.
  • To elucidate the bonding interactions in the resulting gold-alkyne complex.

Main Methods:

  • Single-crystal to single-crystal solid/gas reaction.
  • Synthesis of [Au(L1)(CO)][BArF4] and reaction with acetylene gas.
  • Single crystal X-ray diffraction.
  • Solution and solid-state NMR spectroscopy.
  • Periodic Density Functional Theory (DFT) calculations.

Main Results:

  • Clean synthesis of the gold(I) acetylene complex [Au(L1)(η2-HC≡CH)][BArF4] via solid/gas reaction.
  • Characterization confirmed the structure and bonding.
  • DFT calculations revealed σ-donation, π-backdonation, and dispersion interactions.

Conclusions:

  • Single-crystal to single-crystal solid/gas reactivity provides a viable route to gold-alkyne complexes.
  • The bonding in the gold(I) acetylene complex is multifaceted, involving donation, backdonation, and dispersion forces.
  • This work provides fundamental insights into gold-alkyne interactions.