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Related Concept Videos

SN2 Reaction: Kinetics02:14

SN2 Reaction: Kinetics

10.6K
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...
10.6K
SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

18.2K
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...
18.2K
SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

12.6K
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...
12.6K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

12.4K
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...
12.4K
SN1 Reaction: Kinetics02:05

SN1 Reaction: Kinetics

9.9K
In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...
9.9K
Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

17.6K
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the substrate simultaneously as the leaving group departs, in SN1 reactions, the substrate first dissociates to give the carbocation intermediate. Various factors such as the structure of the substrate, the strength of the nucleophile, and the nature of the solvent promote one mechanism over the other.
With increased substitution on the alkyl halide,...
17.6K

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Dissolution Dynamic Nuclear Polarization Instrumentation for Real-time Enzymatic Reaction Rate Measurements by NMR
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Mode-Specific SN2 Reaction Dynamics.

Yan Wang1,2, Hongwei Song1, István Szabó3

  • 1Key Laboratory of Magnetic Resonance in Biological Systems, National Center for Magnetic Resonance in Wuhan, State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences , Wuhan 430071, China.

The Journal of Physical Chemistry Letters
|August 10, 2016
PubMed
Summary
This summary is machine-generated.

This study investigates the microscopic dynamics of bimolecular nucleophilic substitution (SN2) reactions. It reveals that both direct and indirect mechanisms contribute to reactivity, influenced by reactant vibrational modes.

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Area of Science:

  • Chemical Kinetics
  • Quantum Mechanics
  • Reaction Dynamics

Background:

  • The microscopic dynamics of bimolecular nucleophilic substitution (SN2) reactions remain incompletely understood.
  • Understanding SN2 reaction mechanisms is crucial in various chemical processes.

Purpose of the Study:

  • To elucidate the microscopic dynamics of a prototypical SN2 reaction: F(-) + CH3Cl → CH3F + Cl(-).
  • To investigate the contributions of direct and indirect mechanisms to the reaction.
  • To analyze the influence of reactant vibrational mode excitation on reactivity.

Main Methods:

  • Utilized a high-dimensional quantum mechanical model.
  • Employed an accurate potential energy surface (PES) for calculations.
  • Analyzed reaction dynamics using quasi-classical trajectories (QCT) on the same PES.

Main Results:

  • The indirect mechanism is dominant at low collision energies.
  • The direct mechanism significantly contributes to the overall reactivity.
  • Reactivity exhibits dependence on specific reactant vibrational mode excitation.
  • Mode specificity is more pronounced in the direct reaction pathway.

Conclusions:

  • Both direct and indirect mechanisms play vital roles in SN2 reaction dynamics.
  • Vibrational mode excitation is a key factor determining reactivity and selectivity.
  • A transition-state-based model effectively rationalizes the observed mode specificity.