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

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

Structure of Benzene: Kekulé Model

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.

You might also read

Related Articles

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

Sort by

Same author

Developmental exposure to a human-relevant PCB mixture: impacts on PCB congeners, metabolites, and drug-metabolizing enzymes in the bladder of post-weaning mice.

Archives of toxicology·2026

Same author

Morphological, Behavioral, and Transcriptomic Profiling Reveals Developmental Toxicity of PCB Metabolites in Zebrafish.

Toxics·2026

Same author

Synthesis and Preclinical Evaluation of [<sup>11</sup>C]GNE-0877 as a Potential PET Radioligand for Imaging Brain Leucine-Rich Repeat Kinase 2.

ACS omega·2026

Same author

Neuroprotection Against a Panel of Toxicants via a Novel Analog of the Natural Product Fraxinellone.

Chemical research in toxicology·2026

Same author

BENOXACOR IS ENANTIOSELECTIVELY METABOLIZED BY MICROSOMES AND CYTOSOL FROM THE HUMAN LIVER.

Emerging contaminants·2026

Same author

Emergency Preparedness in Older Adults With and Without COPD During Power Outages and Natural Disasters.

Journal of applied gerontology : the official journal of the Southern Gerontological Society·2026

Search research articles

Related Experiment Video

Updated: Jun 5, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

1,3,5-Trichloro-2-methoxy-benzene.

Sanjay Telu, Sean Parkin, Larry W Robertson

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This summary is machine-generated.

The methoxy group in a chlorinated aromatic compound is twisted out of plane due to bulky chlorine atoms. This structural distortion was quantified using crystallographic analysis.

More Related Videos

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Related Experiment Videos

Last Updated: Jun 5, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

Organic Chemistry
Crystallography

Background:

Understanding the conformational preferences of substituted aromatic compounds is crucial in organic chemistry.
Steric hindrance from substituents can significantly influence molecular geometry.

Purpose of the Study:

To investigate the impact of ortho-chloro substituents on the conformation of the methoxy group in a specific chlorinated aromatic compound.
To determine the precise dihedral angle of the methoxy group relative to the aromatic ring.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
The dihedral angle between the methoxy group and the aromatic ring plane was measured.

Main Results:

The methoxy group was found to be significantly rotated out of the plane of the aromatic ring.
A dihedral angle of 84.11(13)° was measured, indicating a near-perpendicular orientation.
The observed conformation is attributed to steric repulsion from the two ortho-chloro substituents.

Conclusions:

Bulky ortho-substituents can effectively force functional groups out of the aromatic plane.
This study provides a quantitative measure of steric influence on molecular conformation in chlorinated aromatics.