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Related Concept Videos

SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

9.9K
An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
9.9K
SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

11.9K
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism. 
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a...
11.9K
SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

14.4K
The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
14.4K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

9.6K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
9.6K
SN2 Reaction: Kinetics02:14

SN2 Reaction: Kinetics

8.4K
Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
8.4K
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

8.6K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
8.6K

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The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
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The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique

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Accelerating σ-Bond Metathesis at Sn(II) Centers.

Richard Y Kong1, Joseph B Parry1, Guy R Anello1

  • 1Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, 162 Sciences Drive, Ithaca, New York 14853, United States.

Journal of the American Chemical Society
|October 23, 2023
PubMed
Summary

This study developed a tin-nickel catalyst for efficient carbon dioxide hydroboration. Tuning the electronic properties of tin centers enhances catalytic activity, offering a cheaper alternative to transition metals.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Demonstrating the Simplicity and In Situ Temperature Monitoring of the Mechanochemical Synthesis of Metal Chalcogenides Suitable for Thermoelectrics
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Demonstrating the Simplicity and In Situ Temperature Monitoring of the Mechanochemical Synthesis of Metal Chalcogenides Suitable for Thermoelectrics

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The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Demonstrating the Simplicity and In Situ Temperature Monitoring of the Mechanochemical Synthesis of Metal Chalcogenides Suitable for Thermoelectrics
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Demonstrating the Simplicity and In Situ Temperature Monitoring of the Mechanochemical Synthesis of Metal Chalcogenides Suitable for Thermoelectrics

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Area of Science:

  • Catalysis
  • Organometallic Chemistry
  • Materials Science

Background:

  • Molecular main-group hydrides offer cost-effective alternatives to transition-metal catalysts.
  • Ligand tuning in transition metals has led to advanced catalyst development.
  • Understanding electronic structure-activity relationships is key for main-group hydride catalyst improvement.

Purpose of the Study:

  • To develop superior main-group hydride catalysts by understanding electronic structure-activity relationships.
  • To report a modular tin-nickel bimetallic system for systematic ligand variation.
  • To investigate the effect of electronic tuning on tin centers for catalytic applications.

Main Methods:

  • Systematic variation of ancillary ligands on nickel to tune the tin center.
  • Utilizing Tin L1 X-ray absorption spectroscopy (XAS) to measure electron density at the tin center.
  • Developing a tin-based catalyst for carbon dioxide hydroboration using pinacolborane.

Main Results:

  • Increased electron density at tin centers was shown to accelerate the rate of sigma-bond metathesis.
  • A highly active tin-based catalyst for CO2 hydroboration was developed.
  • Engineering London dispersion interactions in the secondary coordination sphere further accelerated the catalytic rate.

Conclusions:

  • The electronics of main-group catalysts can be controlled independently of geometric perturbations.
  • This electronic control leads to substantial differences in catalytic reactivity.
  • The developed Sn-Ni system provides a pathway for designing more efficient main-group catalysts.