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Related Concept Videos

Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.7K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
4.7K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Radical Formation: Overview01:03

Radical Formation: Overview

2.7K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.7K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.7K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

1.9K
Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
1.9K

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Rapid Scan Electron Paramagnetic Resonance Opens New Avenues for Imaging Physiologically Important Parameters In Vivo
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Nitroxide Radical Spin Probes for Exploring Halogen-Bonding Interactions in Solution.

Lorenzo Gualandi1, Elisabetta Mezzina1, Paola Franchi1

  • 1Dipartimento di Chimica "G. Ciamician", University of Bologna, Via S. Giacomo 11, 40126, Bologna, Italy.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 17, 2016
PubMed
Summary
This summary is machine-generated.

Researchers developed a new spin probe, 2,3,5,6-tetrafluoro-4-iodobenzyl tert-butyl nitroxide (2-I), for detecting halogen-bond (XB) complexes using electron paramagnetic resonance (EPR) spectroscopy. This method offers direct quantification of XB bond strength in solution.

Keywords:
electron paramagnetic resonancehalogen bondingnitroxidespin probessupramolecular chemistry

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Area of Science:

  • Supramolecular Chemistry
  • Chemical Physics
  • Analytical Chemistry

Background:

  • Halogen bonding (XB) is a significant non-covalent interaction crucial in molecular recognition and crystal engineering.
  • Direct experimental methods for quantifying XB bond strength in solution are limited.
  • Spin probes offer potential for sensitive detection of molecular interactions.

Purpose of the Study:

  • To synthesize a novel spin probe, 2,3,5,6-tetrafluoro-4-iodobenzyl tert-butyl nitroxide (2-I).
  • To utilize 2-I as an electron paramagnetic resonance (EPR) probe for detecting and quantifying halogen-bond (XB) complexes in solution.
  • To establish a direct EPR methodology for determining XB bond strength.

Main Methods:

  • Synthesis of the 2,3,5,6-tetrafluoro-4-iodobenzyl tert-butyl nitroxide (2-I) spin probe.
  • Detection of XB complex formation by monitoring changes in benzylic hyperfine splitting using EPR spectroscopy.
  • Determination of thermodynamic parameters (e.g., equilibrium constants) via temperature-dependent EPR and competitive binding experiments.

Main Results:

  • Successful synthesis and characterization of the 2-I spin probe.
  • Evidence of XB complex formation between 2-I and various XB acceptors through significant EPR spectral changes.
  • Quantification of thermodynamic parameters for XB complex formation with quinuclidine and a chloride anion.

Conclusions:

  • The developed 2-I spin probe effectively detects halogen-bond complexes in solution via EPR.
  • This methodology provides a direct and reliable means to determine XB bond strength.
  • The study establishes a novel EPR-based approach for quantitative analysis of halogen bonding.