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Related Concept Videos

Solvating Effects02:12

Solvating Effects

An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

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,...
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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 observed.
Ionic Strength: Effects on Chemical Equilibria01:19

Ionic Strength: Effects on Chemical Equilibria

The addition of an inert ionic compound increases the solubility of a sparingly soluble salt. For example, adding potassium nitrate to a saturated solution of calcium sulfate significantly enhances the solubility of calcium sulfate. Le Châtelier's principle cannot predict this shift in the equilibrium. Instead, this could be explained in terms of changes in the effective concentration of the ions in solution in the presence of added inert salt.
In this solution, the primary cation—the calcium...
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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...
SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

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 polar...

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Steric and solvation effects in ionic S(N)2 reactions.

Xin Chen1, Colleen K Regan, Stephen L Craig

  • 1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.

Journal of the American Chemical Society
|October 22, 2009
PubMed
Summary

Solvation effects on S(N)2 reactions show minimal size dependence. Steric hindrance in alkyl chloronitriles is similar in gas and solution phases, suggesting compensated solvation effects.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Steric effects significantly influence reaction rates in organic chemistry.
  • Understanding solvation's role in S(N)2 reactions is crucial for predicting reactivity.

Purpose of the Study:

  • To investigate the contribution of solvation to steric effects in S(N)2 reactions.
  • To compare steric effects in gas and solution phases using alkyl chloronitriles as a model system.

Main Methods:

  • Experimental kinetic studies of chloride ion reactions with alkyl chloronitriles.
  • Theoretical investigations including polarizable continuum models and QM/MM simulations.

Main Results:

  • Increased substitution at the beta-carbon consistently lowered reactivity, indicating steric hindrance.
  • The magnitude of steric hindrance was similar in both gas and solution phases.
  • Solvation energies of transition states showed weak dependence on substituent size.

Conclusions:

  • Solvation does not significantly alter the steric effect in these S(N)2 reactions.
  • Weak size dependence is attributed to compensation between direct shielding and indirect solvation effects.
  • Findings contrast with other ionic systems where solvation strongly depends on size.