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Related Concept Videos

Elimination Reactions02:25

Elimination Reactions

14.6K
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
14.6K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

3.2K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
3.2K
E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

12.2K
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
12.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.2K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.2K
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.7K
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
2.7K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.9K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.9K

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Updated: Oct 20, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Force-modulated reductive elimination from platinum(ii) diaryl complexes.

Yichen Yu1, Chenxu Wang2, Liqi Wang1

  • 1Department of Chemistry, Duke University Durham North Carolina 27708 USA ross.widenhoefer@duke.edu stephen.craig@duke.edu.

Chemical Science
|September 15, 2021
PubMed
Summary
This summary is machine-generated.

Mechanical force applied to spectator ligands can alter transition metal reactivity. Compressive forces slow reactions, while tensile forces accelerate them, offering new avenues for force-modulated catalysis.

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Area of Science:

  • Organometallic Chemistry
  • Mechanochemistry
  • Computational Chemistry

Background:

  • Mechanical forces are known to influence covalent chemical reactions.
  • The impact of force on spectator ligands in transition metal reactivity remains largely uninvestigated.

Purpose of the Study:

  • To quantify the effect of mechanical force on spectator ligands on the rate of reductive elimination in platinum(II) complexes.
  • To explore the relationship between ligand structure, applied force, and reaction kinetics.

Main Methods:

  • Density Functional Theory (DFT) computations to model mechanochemical kinetics.
  • Experimental validation using platinum(II) diaryl complexes with macrocyclic bis(phosphine) ligands.
  • Utilized a macrocyclic force probe ligand coupled to a MeOBiphep-based design.

Main Results:

  • Complex dependence of mechanochemical kinetics on ligand structure was revealed by DFT.
  • Compressive forces decreased reductive elimination rates, while extension forces increased them (3.4-fold change over ~290 pN).
  • Force primarily affects the transition state's O⋯O distance, not the ground state geometry of the platinum complex.

Conclusions:

  • Mechanical force applied to spectator ligands can significantly modulate transition metal reactivity.
  • Demonstrated a method to experimentally map force-induced geometric changes in reaction transition states.
  • Highlights potential for force-modulated catalysis and understanding reaction mechanisms.