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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

16.3K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.3K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Electrophiles02:28

Electrophiles

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This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

31.8K
sp3d and sp3d 2 Hybridization
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.1K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.1K
Halogens03:01

Halogens

18.3K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Dichlorine-pyridine N-oxide halogen-bonded complexes.

Niklas Limberg1, J Mikko Rautiainen2, Jan Lundell2

  • 1Department of Chemistry and Biochemistry, Freie Universität Berlin Fabeckstr. 34/36 14195 Berlin Germany s.riedel@fu-berlin.de.

Chemical Science
|November 4, 2024
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Summary
This summary is machine-generated.

Researchers discovered a new halogen bonding (XB) interaction using dichlorine and N-oxide. These unstable crystalline complexes decompose into hydrogen-bonded structures, revealing insights into halogen bonding dynamics.

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Area of Science:

  • Solid-state chemistry
  • Supramolecular chemistry
  • Crystallography

Background:

  • Halogen bonding (XB) is a significant non-covalent interaction.
  • N-oxides are common XB acceptors.
  • Dichlorine (Cl2) has been explored as a potential XB donor.

Purpose of the Study:

  • To demonstrate and characterize a novel halogen-bonded paradigm using dichlorine as the XB donor and N-oxides as XB acceptors.
  • To investigate the stability and decomposition pathways of these crystalline complexes.
  • To compare the strength of Cl-Cl···O halogen bonds with traditional iodine-based halogen bonds.

Main Methods:

  • Synthesis and crystallization of dichlorine-N-oxide complexes.
  • X-ray diffraction analysis at low temperatures (-196 °C to -80 °C).
  • Analysis of crystalline complex stability and decomposition products.

Main Results:

  • Successful formation of crystalline complexes between dichlorine and N-oxides.
  • Demonstration of Cl-Cl···-O-N+ halogen bonding.
  • Observed high instability of crystalline complexes, leading to decomposition into Cl⋯H-O-N hydrogen-bonded complexes.
  • Normalized XB interaction ratio (RXB) for Cl⋯O interactions comparable to traditional I⋯O interactions.
  • Cl-Cl···O XB angles ranging from 172° to 177°, indicating structure-guiding influence of the chlorine σ-hole.

Conclusions:

  • A new halogen-bonded paradigm involving dichlorine and N-oxides has been established.
  • The study highlights the transient nature and decomposition pathways of these novel halogen-bonded complexes.
  • The findings underscore the potential of chlorine as an effective halogen bond donor, comparable to iodine in certain systems.