Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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...

Mass Spectrometry: Alkyl Halide Fragmentation

Mass Spectrometry: Alkyl Halide Fragmentation

Chlorine isotopes exist as 35Cl and 37Cl in a 3:1 ratio, while bromine isotopes exist as 79Br and 81Br in a 1:1 ratio. The mass spectrum of alkyl halides typically produces two distinct molecular ion peaks, the molecular ion peak, [M], and the molecular ion plus two, [M + 2] peak. The relative heights of these two peaks are proportional to the isotopic abundance ratios of the halide. For example, 2‐chloropropane and 1‐bromopropane display two peaks with relative peak heights in a 3:1 and...

SN1 Reaction: Mechanism

S_N1 Reaction: Mechanism

Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism.
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a...

E1 Reaction: Kinetics and Mechanism

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...

Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...

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.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Study on Thermal Stability, Phase Transition Characteristics, and Pyrolysis Product Distributions of Long-Chain n-Alkanes (C12-C15).

Molecules (Basel, Switzerland)·2026

Same author

Stereoselective <i>C</i>-Aryl and <i>C</i>-Vinyl Glycosylation via Iron-Catalyzed Reductive Coupling.

Organic letters·2026

Same author

Excellent Ferroelectricity and Thermal Stability in Ce-Doped HfO<sub>2</sub> Thin Films via Oxygen Vacancy Modulation.

ACS applied materials & interfaces·2026

Same author

Large Magnetoresistance in a Si-Based Double-Tunnel Junction with Purely Organic Radical Molecules.

Nano letters·2026

Same author

Temperature-responsive gelatin-based composite hydrogel pads with smart controlled phage release for intelligent antimicrobial packaging in chicken preservation.

Food research international (Ottawa, Ont.)·2026

Same author

Dissipative quantum geometric phase in the spin-boson system.

The Journal of chemical physics·2026

Search research articles

Related Experiment Video

Updated: Aug 12, 2025

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F−

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F⁻

Published on: July 27, 2018

Solvent Dynamics of Aqueous Halides before and after Photoionization.

Marco Reidelbach^1,2, Mei Bai^2,3, Michaela Schneeberger^1,2

¹Department of Chemistry, Universität Hamburg, Harbor Bldg. 610, Luruper Chaussee 149, 22761Hamburg, Germany.

The Journal of Physical Chemistry. B

|February 2, 2023

Summary

We simulated photoionization of halide ions in water using quantum mechanical/molecular mechanical (QM/MM) and classical molecular dynamics (MD) methods. QM/MM simulations accurately predicted extended X-ray absorption fine structure (EXAFS) spectra, revealing solvent dynamics crucial for electron transfer reactions.

More Related Videos

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

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

Published on: May 29, 2018

Related Experiment Videos

Last Updated: Aug 12, 2025

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F−

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F⁻

Published on: July 27, 2018

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

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

Published on: May 29, 2018

Area of Science:

Physical Chemistry
Computational Chemistry
Spectroscopy

Background:

Solvent dynamics significantly impact electron transfer reactions.
Photoionization of halide ions in water serves as a model system to study these effects.
Absence of internal solute nuclear degrees of freedom allows unique identification of solvent dynamics.

Purpose of the Study:

To compare quantum mechanical/molecular mechanical (QM/MM) and classical molecular dynamics (MD) methods in simulating solvent dynamics.
To calculate and analyze extended X-ray absorption fine structure (EXAFS) spectra for halide ions and their neutral atoms in water.
To assess the reliability of simulation methods for elucidating solvent dynamics through EXAFS analysis.

Main Methods:

Simulated equilibrium solvent dynamics using QM/MM and classical MD.
Calculated EXAFS spectra rigorously from MD snapshots.
Compared simulated EXAFS spectra with experimental and literature data.

Main Results:

QM/MM MD simulations yielded EXAFS spectra in good agreement with experimental data for halide ions.
Classical MD simulations matched the oscillatory period but overestimated the amplitude of EXAFS spectra for ions.
Classical MD failed qualitatively for neutral halogen atoms, significantly affecting both period and amplitude of EXAFS spectra.

Conclusions:

QM/MM-based EXAFS simulations demonstrate high reliability for studying solvent dynamics.
EXAFS spectral analysis, considering both amplitude and oscillatory period, is crucial for evaluating simulation methods.
Combined theoretical and experimental EXAFS approaches are effective for elucidating nonequilibrium solvent dynamics in photoionization and electron transfer reactions.