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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...

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.

Predicting Molecular Geometry

Predicting Molecular Geometry

VSEPR Theory for Determination of Electron Pair Geometries

Lewis Structures of Molecular Compounds and Polyatomic Ions

Lewis Structures of Molecular Compounds and Polyatomic Ions

To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:

π Molecular Orbitals of the Allyl Cation and Anion

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...

Ionic Crystal Structures

Ionic Crystal Structures

Ionic crystals consist of two or more different kinds of ions that usually have different sizes. The packing of these ions into a crystal structure is more complex than the packing of metal atoms that are the same size.
Most monatomic ions behave as charged spheres, and their attraction for ions of opposite charge is the same in every direction. Consequently, stable structures for ionic compounds result (1) when ions of one charge are surrounded by as many ions as possible of the opposite...

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Related Experiment Video

Updated: Oct 11, 2025

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

Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids.

Brianna O'Rourke¹, Clare Lauderback¹, Lara I Teodoro¹

¹Department of Chemistry and Physics, Ave Maria University, Ave Maria, Florida 34142, United States.

|December 6, 2021

Summary

Researchers synthesized novel triphenylphosphonium-based ionic liquids (ILs) with high thermal stability up to 450 °C. Structural analysis correlated intermolecular interactions with thermal properties, aiding rational material design.

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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

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Published on: October 10, 2016

Area of Science:

Materials Science
Supramolecular Chemistry
Physical Chemistry

Background:

Ionic liquids (ILs) are versatile materials with broad applications in energy, materials, and medicine.
Rational design of novel ionic liquids remains a significant challenge.
Triphenylphosphonium-based compounds offer potential for unique properties.

Purpose of the Study:

To synthesize and characterize novel triphenylphosphonium-based ionic liquids.
To investigate the relationship between solid-state structure, intermolecular interactions, and thermal properties.
To provide insights into the rational design of ionic liquids with tailored properties.

Main Methods:

Synthesis of four new triphenylphosphonium-based ionic liquids.
Single-crystal X-ray diffraction for solid-state structure determination.
Hirshfeld surface analysis to study intermolecular interactions.
Computational methods to analyze cation alkyl chain arrangements.
Thermal analysis (DSC/TGA) to determine melting points, phase transitions, and decomposition temperatures.

Main Results:

Successfully synthesized four novel triphenylphosphonium-based ionic liquids.
Compounds exhibited high thermal stability with decomposition temperatures up to 450 °C.
Anion geometry significantly influenced cation-anion interactions in the crystalline state.
Intermolecular interactions correlated with observed melting points and phase transitions.
Computational analysis provided insights into the role of alkyl chain rotational freedom on thermal behavior.

Conclusions:

The study successfully established a structure-property relationship for novel triphenylphosphonium-based ionic liquids.
Understanding intermolecular interactions is crucial for the rational design of thermally stable ionic liquids.
These findings contribute to the expanding library of ionic liquids with unique property profiles for diverse applications.