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Halogenation of Alkenes

Halogenation of Alkenes

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.

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

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...

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...

Electrophilic Addition to Alkynes: Halogenation

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.

VSEPR Theory and the Effect of Lone Pairs

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry

Hydrogen Bonds

Hydrogen Bonds

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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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

Asymmetric bifurcated halogen bonds.

Martin Novák¹, Cina Foroutan-Nejad, Radek Marek

¹CEITEC - Central European Institute of Technology, Masaryk University, Kamenice 5/A4, CZ-625 00 Brno, Czech Republic. 119499@mail.muni.cz radek.marek@ceitec.muni.cz.

Physical Chemistry Chemical Physics : PCCP

|February 7, 2015

Summary

This study details asymmetric halogen bonding (XB) using DFT analysis. The findings reveal electrostatic and non-electrostatic factors are comparable, influencing the interaction strength with electron donor molecules.

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Area of Science:

Supramolecular Chemistry
Computational Chemistry
Organic Chemistry

Background:

Halogen bonding (XB) is crucial in materials science and drug design.
The precise nature of XB interactions remains under investigation.
Understanding XB is key to advancing chemical applications.

Purpose of the Study:

To perform a detailed DFT analysis of three-center asymmetric halogen bonds.
To investigate the nature of XB interactions between dihalogen molecules and substituted benzene.
To explore the influence of electron donor charge on XB.

Main Methods:

Density Functional Theory (DFT) analysis.
Energy decomposition analysis.
Orbital and electron density analyses.

Main Results:

Electrostatic and non-electrostatic stabilization contributions are comparable in asymmetric XB.
Interaction strength increases with the electron donor molecule's negative charge.
Bifurcated halogen bonds (BXB) were observed, deviating from the standard XB definition.

Conclusions:

The study provides insights into the complex nature of asymmetric halogen bonding.
The findings suggest a re-evaluation of XB classification, proposing the term 'bifurcated halogen bond'.
This research contributes to a deeper understanding of non-covalent interactions.