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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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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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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
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Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding.

Patrick Wonner1, Lukas Vogel1, Maximilian Düser1

  • 1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.

Angewandte Chemie (International Ed. in English)
|June 13, 2017
PubMed
Summary
This summary is machine-generated.

Selenium-based chalcogen bond donors show promise as Lewis acids in organic synthesis. These novel donors accelerate reactions like benzhydryl bromide solvolysis more effectively than traditional halogen bond donors.

Keywords:
Lewis acidschalcogen bondingchalcogensnoncovalent interactionssolvolysis

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Noncovalent Interactions

Background:

  • Chalcogen bonding is an under-explored noncovalent interaction analogous to halogen bonding.
  • The application of chalcogen bonding in catalysis and organic synthesis remains limited.

Purpose of the Study:

  • To investigate the first application of selenium-based chalcogen bond donors as Lewis acids in organic synthesis.
  • To evaluate the efficacy of these donors in promoting chemical reactions.

Main Methods:

  • The solvolysis of benzhydryl bromide was employed as a benchmark halide abstraction reaction.
  • Comparative experiments were conducted using chalcogen bond donors with a bis(benzimidazolium) core and a brominated halogen bond donor.

Main Results:

  • Chalcogen bond donors accelerated the reaction rate by a factor of 20-30 compared to background reactivity.
  • Evidence suggests the observed rate acceleration is attributable to chalcogen bonding interactions.
  • The selenium-based chalcogen bond donors outperformed a related brominated halogen bond donor.

Conclusions:

  • Selenium-based chalcogen bonding represents a novel and effective Lewis acid activation strategy in organic synthesis.
  • This study highlights the potential of chalcogen bonding as a powerful tool for chemical transformations.
  • Chalcogen bond donors offer a promising alternative to halogen bond donors in catalytic applications.