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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

16.6K
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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Halogens03:01

Halogens

17.2K
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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Halogenation of Alkenes02:46

Halogenation of Alkenes

16.9K
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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Hydrogen Bonds01:04

Hydrogen Bonds

11.8K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Hydrogen Bonds00:26

Hydrogen Bonds

109.2K
Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

7.3K
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.
7.3K

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Updated: Apr 26, 2026

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

71.2K

Type II halogen···halogen contacts are halogen bonds.

Pierangelo Metrangolo1, Giuseppe Resnati1

  • 1Laboratory of Nanostructured Fluorinated Materials of the Department of Chemistry, Materials and Chemical Engineering "Giulio Natta", Politecnico di Milano , Via L. Mancinelli 7, Milano, 20131, Italy.

Iucrj
|July 31, 2014
PubMed
Summary
This summary is machine-generated.

Halogen bonds in dihalophenols differ chemically. Only type II halogen···halogen contacts meet the IUPAC definition of true halogen bonds, distinguishing them from type I interactions.

Keywords:
halogen bondshalogenated phenols

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Area of Science:

  • Chemistry
  • Crystallography

Background:

  • Halogen bonding is a significant non-covalent interaction in chemistry.
  • Distinguishing between different types of halogen···halogen contacts is crucial for understanding their nature.

Purpose of the Study:

  • To investigate the chemical nature of type I and type II halogen···halogen contacts in dihalophenols.
  • To determine which types of contacts align with the IUPAC definition of halogen bonds.

Main Methods:

  • Synthesis and crystallographic analysis of a series of dihalophenols with varying halogen substitutions (Cl, Br, I).
  • Computational analysis to probe the electronic and geometric characteristics of halogen···halogen contacts.

Main Results:

  • Type I and type II halogen···halogen contacts exhibit distinct chemical properties.
  • Type II contacts, characterized by specific geometric and electronic features, satisfy the criteria for true halogen bonds as defined by IUPAC.
  • Type I contacts do not meet the stringent requirements of the IUPAC definition.

Conclusions:

  • The study differentiates between various halogen···halogen interactions in dihalophenols.
  • Only type II halogen···halogen contacts are confirmed as genuine halogen bonds, based on the current IUPAC definition.