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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...
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.
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.
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only in the...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Related Experiment Video

Updated: May 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Ab initio study of weakly bound halogen complexes: RX⋯PH3.

Herbert C Georg1, Eudes E Fileti, Thaciana Malaspina

  • 1Instituto de Física, Universidade Federal de Goiás, CP 131, 74001-970, Goiânia, Goiás, Brazil.

Journal of Molecular Modeling
|August 17, 2012
PubMed
Summary

This study reveals how ipso carbon hybridization influences halogen bonding interactions between halogenated compounds and phosphine. Stronger interactions were observed with heavier halogens, impacting complex stability and electrical properties.

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

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Last Updated: May 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

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

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Molecular Interactions

Background:

  • Halogen bonding is a significant non-covalent interaction.
  • Understanding the role of carbon hybridization in these interactions is crucial.
  • Previous studies have not fully explored the impact of ipso carbon hybridization on halogen bonding with phosphorus.

Purpose of the Study:

  • To investigate the influence of ipso carbon hybridization on halogen bonding.
  • To analyze the interaction between halogenated compounds (RX) and phosphine (PH3).
  • To determine the effect of different halogens (F, Cl, Br, I) and R groups (methyl, phenyl, acetyl, H) on complex stability and properties.

Main Methods:

  • Ab initio calculations using MP2, MP4, and CCSD(T) methods.
  • Energy analysis to quantify interaction strengths.
  • Electrostatic potential mapping and Natural Bond Orbital (NBO) analysis for charge transfer insights.
  • Determination of electrical properties, including dipole and polarizability.

Main Results:

  • Interaction energies ranged from -4.14 to -11.92 kJ mol(-1) at the MP2 level.
  • Electronic correlation significantly affects interaction energies, with reductions up to 27% observed at higher levels.
  • PhCl⋯PH3 and MeX⋯PH3 complexes were found to be unstable.
  • Charge transfer increased with heavier halogens (I > Br > Cl).
  • A systematic increase in dipole polarizability (0.7-6.7 u.a.) was observed due to interaction.

Conclusions:

  • Ipso carbon hybridization plays a key role in modulating halogen bonding strength.
  • Heavier halogens and specific R groups lead to more stable complexes and greater charge transfer.
  • These interactions significantly influence the electrical properties, particularly dipole polarizability, of the studied complexes.