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Alkyl Halides

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...

ortho–para-Directing Deactivators: Halogens

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...

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...

Halogens

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.

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Updated: May 2, 2026

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

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

Published on: March 24, 2018

Aromatic superhalogens.

Brandon Z Child¹, Santanab Giri, Scott Gronert

¹Physics Department, Virginia Commonwealth University, Richmond, VA 23284 (USA).

Chemistry (Weinheim an Der Bergstrasse, Germany)

|March 20, 2014

Summary

This summary is machine-generated.

Researchers designed novel organic molecules with exceptionally high electron affinities, surpassing those of halogens. These findings introduce a new category of superhalogens without metals or halogens.

Keywords:

aromaticity density functional calculations electron affinity electronegative species superhalogens

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

Organic Chemistry
Computational Chemistry
Materials Science

Background:

Organic molecules typically exhibit electron affinities lower than those of halogens.
Designing molecules with high electron affinities is crucial for advanced applications.

Purpose of the Study:

To explore the potential of aromaticity rules in designing organic molecules with enhanced electron affinities.
To investigate novel superhalogens composed solely of organic elements.

Main Methods:

Utilized density functional theory (DFT) calculations.
Employed molecular design strategies based on aromaticity principles, including ligand tailoring of cyclopentadienyl and benzoannulation.
Incorporated isoelectronic nitrogen atom substitutions for carbon-hydrogen groups.

Main Results:

Identified organic molecules with electron affinities significantly exceeding those of halogen atoms.
Achieved calculated electron affinities as high as 5.59 eV for designed molecules.
Demonstrated the feasibility of creating superhalogens from organic components.

Conclusions:

Aromaticity rules provide a powerful framework for designing high-electron-affinity organic molecules.
This research opens avenues for a new class of metal-free and halogen-free superhalogens.
The designed molecules hold potential for applications requiring strong electron acceptors.