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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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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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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.
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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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Boronyl-Based Polycyclic Superhalogens.

Ambrish Kumar Srivastava1

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

The Journal of Physical Chemistry. A
|November 30, 2023
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Summary
This summary is machine-generated.

Researchers explored boronyl (BO) substituted polycyclic hydrocarbons as potential superhalogens. These new boronyl-based polycyclic superhalogens exhibit higher electron affinity and vertical detachment energy than their cyano analogs.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Quantum Chemistry

Background:

  • Superhalogenity is defined by high electron affinity (EA) in radicals or vertical detachment energy (VDE) in anions compared to halogens/halides.
  • Previous work demonstrated polycyclic superhalogens (PSs) by substituting cyano (CN) groups in polycyclic hydrocarbons (PHs), noting a link between superhalogenity and aromaticity.
  • Boronyl (BO) groups are isoelectronic and inorganic analogs to CN groups, prompting investigation into their potential in creating superhalogens.

Purpose of the Study:

  • To investigate the potential of substituting boronyl (BO) groups in polycyclic hydrocarbons (PHs) to create new polycyclic superhalogens (PSs).
  • To compare the superhalogen properties of BO-based PSs with existing cyanide (CN)-based PSs.
  • To explore the relationship between aromaticity and superhalogenity in these novel BO-substituted systems.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to study the electronic properties of BO-substituted PHs.
  • Calculations included determining vertical detachment energies (VDEs) for anions and electron affinities (EAs) for radicals.
  • Structural and aromaticity analyses were performed for both BO- and CN-substituted polycyclic systems.

Main Results:

  • BO-substituted C5H5- anions (C5H5- (BO)n-) exhibit superhalogen properties for n ≥ 3, similar to their CN analogs.
  • Unlike CN-based systems, the superhalogenity of BO-based anions does not directly correlate with their aromaticity.
  • BO-substituted polycyclic anions show significantly higher VDEs and their radicals show higher EAs (exceeding 5 eV) compared to their CN-based counterparts, despite reduced aromaticity.

Conclusions:

  • A new class of boronyl-based polycyclic superhalogens has been proposed.
  • These BO-based superhalogens offer enhanced electronic properties (VDE and EA) compared to CN-based superhalogens.
  • The findings suggest potential for synthetic chemists and experimentalists to explore these novel boronyl-based superhalogen anions.