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Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

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Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
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E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

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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...
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Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

13.4K
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,...
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

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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:
11.7K
Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

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Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
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Investigating Substituent Interactions with Cationic Catalysts.

Ziyuan Gong1, Alberto Smith1, Abdikani Omar Farah2

  • 1Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, GSRC 109, Columbia, South Carolina 29206, United States.

The Journal of Organic Chemistry
|November 22, 2023
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Summary
This summary is machine-generated.

Catalyst delocalization impacts reaction rates by altering interactions with aryl groups. Fused ring catalysts show enhanced interactions, influencing reaction speed and aiding organocatalysis development.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Isothiourea derivatives are effective catalysts for silylation and acylation reactions.
  • Understanding catalyst-substrate interactions is crucial for developing efficient organocatalysts.

Purpose of the Study:

  • To investigate how catalyst structure influences intermolecular interactions in isothiourea-catalyzed reactions.
  • To explore the effect of electronic substituents on aryl groups and catalyst delocalization on reaction rates.

Main Methods:

  • Kinetic studies of silylation and acylation reactions using various aryl-substituted substrates.
  • Employing three catalysts: N-methylimidazole and two isothioureas with differing delocalization abilities.
  • Density Functional Theory (DFT) calculations to model catalyst-substrate interactions.

Main Results:

  • Increased catalyst delocalization reduced sensitivity to aryl group electronics.
  • An isothiourea with a fused benzene ring exhibited significant interactions with lone-pair-containing groups, enhancing reaction rates.
  • DFT studies confirmed interactions between the isothiourea, aryl ring, and alcohol substrate during acylation.
  • Electron-rich or lone-pair-bearing groups stabilized the cationic catalyst, accelerating reactions.

Conclusions:

  • Catalyst delocalization and specific structural features (e.g., fused rings) are key determinants of reactivity in isothiourea-catalyzed reactions.
  • Intermolecular interactions, particularly with electron-rich functional groups, play a significant role in stabilizing transition states and accelerating reactions.
  • Understanding these interactions is vital for the rational design of new organocatalysts.