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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

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...
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

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...
Halogens03:01

Halogens

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.
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction at the stage of...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

Superhalogen anions utilizing acidic functional groups as ligands.

Iwona Anusiewicz1

  • 1Department of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland. iwonaa@chem.univ.gda.pl

The Journal of Physical Chemistry. A
|October 16, 2009
PubMed
Summary
This summary is machine-generated.

Superhalogen anions featuring acidic functional groups exhibit electronic stabilities over 4 eV. Perchlorate ligands yield the highest vertical electron detachment energies (VDE), indicating strong electron binding.

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Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Quantum Chemistry

Background:

  • Superhalogens are anionic species with electron binding energies exceeding those of typical halogens.
  • Understanding the stability and electronic properties of superhalogen anions is crucial for designing novel materials and chemical processes.

Purpose of the Study:

  • To investigate the vertical electron detachment energies (VDE) of NaL(2)(-) and MgL(3)(-) anions with various acidic functional groups (L).
  • To explore the relationship between ligand properties and the electronic stability of superhalogen anions.

Main Methods:

  • Calculations were performed using the outer valence Green function (OVGF) method.
  • The 6-311++G(3df,3pd) basis set was employed for high-accuracy electronic structure calculations.

Main Results:

  • Various acidic functional groups, including perchlorate (-ClO(4)) and nitrate (-NO(3)), were identified as effective ligands for superhalogen anions.
  • Electronic stabilities of these superhalogen anions consistently exceeded 4 eV.
  • Anions with perchlorate ligands exhibited the highest VDE values, ranging from 7.8 to 8.9 eV.
  • Dependencies of VDE on the acid strength, chemical composition of functional groups, and central atom electronegativity were observed.

Conclusions:

  • Acidic functional groups can effectively stabilize superhalogen anions.
  • The electronic properties of superhalogen anions are tunable based on the choice of ligand.
  • Perchlorate-containing anions represent a particularly stable class of superhalogens with significant electron binding energies.