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Related Concept Videos

E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

14.2K
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...
14.2K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

18.3K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
18.3K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Elimination Reactions02:25

Elimination Reactions

18.1K
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...
18.1K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

13.0K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
13.0K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

15.1K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
15.1K

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Stereoelectronic Effects in Cl2 Elimination from Binuclear Pt(III) Complexes.

David C Powers1,2, Seung Jun Hwang1, Bryce L Anderson1

  • 1Department of Chemistry and Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.

Inorganic Chemistry
|November 1, 2016
PubMed
Summary

Platinum(III) complexes efficiently store energy via halogen photoelimination. Stereochemistry significantly impacts this process, guiding strategies for enhanced energy storage in metal-catalyzed reactions.

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Area of Science:

  • Inorganic Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Halogen photoelimination is a key energy-storing step in metal-catalyzed HX-splitting photocycles.
  • Binuclear Platinum(III) complexes are known for high quantum efficiencies in halogen elimination.

Purpose of the Study:

  • To investigate the mechanism and energetics of halogen elimination in binuclear Platinum(III) complexes.
  • To explore the influence of stereochemistry on halogen photoelimination efficiency.

Main Methods:

  • Transient absorption spectroscopy
  • Steady-state photocrystallography
  • Far-infrared vibrational spectroscopy
  • Solution-phase calorimetry

Main Results:

  • A two-step halogen-atom-extrusion mechanism was proposed for meridional Platinum(III) trichlorides.
  • Photoelimination efficiency decreased with increasing Pt-X bond strength.
  • Facial isomers showed higher photoelimination efficiency than predicted by thermochemistry, highlighting stereochemical effects.

Conclusions:

  • Stereochemistry plays a crucial role in the efficiency of halogen elimination reactions.
  • Understanding these stereochemical effects can lead to mechanism-based strategies for efficient, energy-storing halogen elimination.