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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Relative Reactivity of Carboxylic Acid Derivatives01:13

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Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

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The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Strain-Modulated Reactivity: An Acidic Silane.

Serhii Tretiakov1, Léon Witteman1, Martin Lutz2

  • 1Utrecht University, Organic Chemistry & Catalysis, Institution Debye Institute for Nanomaterials Science, Faculty of Science, 3584 CG, Utrecht, The Netherlands.

Angewandte Chemie (International Ed. in English)
|January 21, 2021
PubMed
Summary
This summary is machine-generated.

Researchers developed a strained silicon compound, [TSMPSiH]+, exhibiting unusual acidity due to ring strain. This discovery opens new avenues for developing earth-abundant catalysts with unique reactivity, mimicking transition metals.

Keywords:
aciditysilanessiliconstrained moleculeszwitterions

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Main-group Element Chemistry

Background:

  • Main-group element compounds, particularly silicon, are promising for developing green and cost-effective catalysts.
  • Achieving reactivity comparable to transition metals requires unlocking novel reaction pathways, often through molecular strain.
  • The development of strained silicon compounds is crucial for expanding their catalytic applications.

Purpose of the Study:

  • To synthesize and characterize a strained cationic silane, [TSMPSiH]+, using a tris(2-skatyl)methylphosphonium ([TSMPH3]+) scaffold.
  • To investigate the unusual Si-H bond character and acidity of the synthesized silane.
  • To explore the catalytic potential and reaction mechanisms involving the strained silane and its conjugate base.

Main Methods:

  • Synthesis of the strained cationic silane [TSMPSiH]+.
  • Experimental determination of the pKa in DMSO to quantify its acidity.
  • Mechanistic studies to elucidate the role of ring strain, inductive, and electrostatic effects on acidity.
  • Investigation of the reaction of the conjugate base (TSMPSi) with THF and CH-acids.

Main Results:

  • The strained cationic silane [TSMPSiH]+ exhibits a remarkably acidic Si-H bond (pK a DMSO 4.7–8.1), significantly lower than typical hydrosilanes and even phenol or benzoic acid.
  • Ring strain, alongside inductive and electrostatic effects, is identified as a major contributor to this unusual acidity.
  • The conjugate base TSMPSi, in the presence of CH-acids, activates THF, leading to a fluxional alkoxysilane.
  • The reaction proceeds via trace amounts of [TSMPSiH]+ acting as a strain-release Lewis acid, involving a formal Si(II) to Si(IV) oxidation state change.

Conclusions:

  • Strained silicon compounds can exhibit unprecedented reactivity, challenging the conventional understanding of Si-H bond properties.
  • The observed acidity and catalytic activity highlight the potential of strained main-group compounds as alternatives to transition metal catalysts.
  • This work presents a novel reaction pathway with similarities to transition-metal-mediated processes, opening new avenues in catalysis.