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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.
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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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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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Single-Molecule Fluorescence Visualization of DNA Polymerase Dynamics at G-Quadruplexes
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Templating and Catalyzing [2+2] Photocycloaddition in Solution Using a Dynamic G-Quadruplex.

Keith B Sutyak1, Wes Lee1, Peter V Zavalij1

  • 1Department of Chemistry and Biotechnology, University of Maryland, College Park, MD, 20742, USA.

Angewandte Chemie (International Ed. in English)
|November 6, 2018
PubMed
Summary

This study introduces a novel method for creating cyclobutanes using a G-quadruplex DNA template. This photochemical reaction is highly efficient and selective, offering a new pathway for molecular synthesis.

Keywords:
G-quadruplexONIOM (QM:MM)photochemistryself-assemblysupramolecular catalysistemplated synthesis

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Area of Science:

  • Supramolecular Chemistry
  • Photochemistry
  • Nucleic Acid Chemistry

Background:

  • G-quadruplex DNA structures offer unique scaffolds for molecular assembly.
  • Photochemical [2+2] cycloaddition is a powerful tool for forming cyclobutane rings.
  • Controlling reactivity within noncovalent assemblies remains a challenge.

Purpose of the Study:

  • To develop a templating strategy for photochemical cyclobutane formation.
  • To enable the synthesis of multiple cyclobutanes within a single noncovalent assembly.
  • To investigate the mechanism and efficiency of this novel reaction.

Main Methods:

  • Utilized a G-quadruplex formed by 5'-cinnamate guanosine units and potassium ions (K+).
  • Employed photochemical [2+2] cycloaddition to induce cyclobutane formation.
  • Characterized the reaction using experimental methods and quantum mechanical/molecular mechanics (ONIOM) calculations.

Main Results:

  • Achieved the formation of 8 cyclobutanes in one noncovalent assembly.
  • The reaction proceeded with high yields (>90%).
  • Demonstrated high regio- and diastereoselectivity in the cyclobutane formation.

Conclusions:

  • The templating/covalent capture strategy enables efficient photochemical synthesis of cyclobutanes.
  • The G-quadruplex acts as a precise scaffold, positioning reactive groups for selective cycloaddition.
  • The catalytic nature of the reaction in K+ highlights the dynamic and reversible aspects of the assembly.