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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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SN2 Reaction: Kinetics02:14

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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...
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SN2 Reaction: Mechanism02:27

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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...
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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.
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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

11.6K
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.
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2-Sulfanylhydroquinone Dimer as a Switchable Fluorescent Dye.

Akio Kamimura1, Sanshiro Sakamoto1, Haruka Umemoto1

  • 1Department Applied Chemistry, Yamaguchi University, Ube, 755-8611, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 17, 2019
PubMed
Summary

Researchers developed a novel fluorescent dye whose properties are chemically tunable. Acylation levels of 2-sulfanylhydroquinone dimers control fluorescence, enabling applications as a chemical reaction-responsive dye.

Keywords:
2-sulfanylhydroquinone dimeracylationbiarylsfluorescencehydrolysis

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Photoluminescent dyes are crucial for various sensing and imaging applications.
  • Controlling photoluminescence through chemical stimuli offers advanced functionality.
  • 2-sulfanylhydroquinone dimers present a potential scaffold for responsive dyes.

Purpose of the Study:

  • To develop a novel dye with chemically controllable photoluminescence.
  • To investigate the relationship between acylation of 2-sulfanylhydroquinone dimers and their fluorescence properties.
  • To design a fluorescence-switching dye responsive to chemical reactions.

Main Methods:

  • Synthesis of 2-sulfanylhydroquinone dimers with varying degrees of hydroxyl group acylation.
  • Characterization of photoluminescence properties (fluorescence intensity and wavelength) of the synthesized compounds.
  • Evaluation of the effect of chemical reactions (acylation) on the fluorescence output.

Main Results:

  • Unprotected and monoacylated 2-sulfanylhydroquinone dimers exhibit strong fluorescence.
  • Diacylated and tetraacylated derivatives show significantly quenched fluorescence.
  • A monomesylated derivative demonstrated reversible fluorescence switching upon chemical modification.

Conclusions:

  • The degree of hydroxyl group acylation in 2-sulfanylhydroquinone dimers directly modulates their fluorescence.
  • These findings establish a basis for designing chemical reaction-responsive fluorescent materials.
  • The developed monomesylated derivative functions as a promising fluorescence-switching dye.