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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

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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 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.
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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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.
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sp3d and sp3d 2 Hybridization
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Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Radical Substitution: Allylic Chlorination01:31

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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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A Simple Strategy to Design Polycyclic Superhalogens.

Ambrish Kumar Srivastava1

  • 1Department of Physics, Deen Dayal Upadhyaya Gorakhpur University, Gorakhpur 223009, Uttar Pradesh, India.

The Journal of Physical Chemistry. A
|May 24, 2023
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Summary
This summary is machine-generated.

Researchers designed novel polycyclic superhalogens (PSs) by replacing hydrogens with cyano groups. These superhalogens exhibit significantly enhanced electron affinity and vertical detachment energy, exceeding 5 eV, paving the way for new materials.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Quantum Chemistry

Background:

  • Polycyclic hydrocarbons (PHs) typically have low electron affinity (EA) and vertical detachment energy (VDE) due to their inherent stability.
  • Superhalogens are defined by EA/VDE exceeding that of halogens/halides, offering unique electronic properties.

Purpose of the Study:

  • To develop a strategy for designing polycyclic superhalogens (PSs).
  • To investigate the electronic properties and stability of cyano-substituted polycyclic systems.
  • To assess the feasibility of synthesizing these novel superhalogen compounds.

Main Methods:

  • Density functional theory (DFT) calculations were employed.
  • Investigated the electronic structure and stability of polycyclic systems with cyano substitutions.
  • Analyzed electron affinity (EA) and vertical detachment energy (VDE) of the designed molecules.

Main Results:

  • Polycyclic superhalogens (PSs) with cyano (CN) groups demonstrated significantly enhanced EA and VDE (>5 eV).
  • Most PS anions were aromatic, with one exception (C11(CN)7-) exhibiting anti-aromaticity.
  • The superhalogen property is linked to the EA of CN ligands and charge delocalization, correlating with aromaticity.

Conclusions:

  • The cyano substitution strategy effectively creates polycyclic superhalogens.
  • The calculated properties suggest these compounds are energetically favorable and experimentally viable.
  • Findings encourage experimental synthesis for exploring applications of these novel superhalogens.