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

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

Acidity and Basicity of Alcohols and Phenols

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

Structure and Nomenclature of Alcohols and Phenols

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...

Oxidation of Phenols to Quinones

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

You might also read

Related Articles

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

Sort by

Same author

Dichlorido{μ(3)-6,6'-dieth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}octa-methyldi-μ(3)-oxido-tetra-tin(IV).

Acta crystallographica. Section E, Structure reports online·2011

Same author

9-{4-[(E)-2-(4,6-Dimethyl-1,3,5-triazin-2-yl)ethen-yl]phen-yl}-9H-carbazole.

Acta crystallographica. Section E, Structure reports online·2011

Same author

2-(3,5-Di-tert-butyl-4-hydroxy-benzyl-sulfan-yl)-N'-(3-methoxy-benzyl-idene)acetohydrazide.

Acta crystallographica. Section E, Structure reports online·2011

Same author

Methyl 3-dehydr-oxy-3-oxoursolate.

Acta crystallographica. Section E, Structure reports online·2011

Same author

Methyl 3-acet-oxy-3-dehydroxy-ursolate.

Acta crystallographica. Section E, Structure reports online·2011

Same author

(E)-2,4-Dihydroxy-benzaldehyde 4-ethyl-thio-semicarbazone-4,4'-bipyridine-water (4/7/2).

Acta crystallographica. Section E, Structure reports online·2011

Same journal

Crystal structure of 1-(piperidin-1-yl)butane-1,3-dione.

Acta crystallographica. Section E, Structure reports online·2015

Same journal

Crystal structure of methyl 1-methyl-3,5-diphenyl-7-tosyl-3,6,7,11b-tetra-hydro-pyrazolo-[4',3':5,6]pyrano[3,4-c]quinoline-5a(5H)-carboxyl-ate.

Acta crystallographica. Section E, Structure reports online·2015

Same journal

Crystal structure of 4-amino-1-(4-methyl-benz-yl)pyridinium bromide.

Acta crystallographica. Section E, Structure reports online·2015

Same journal

Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

Acta crystallographica. Section E, Structure reports online·2015

Same journal

Crystal structure of bis-(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate.

Acta crystallographica. Section E, Structure reports online·2015

Same journal

Crystal structure of 2-(di-phenyl-phos-phanyl)phenyl 4-(hy-droxy-meth-yl)benzoate.

Acta crystallographica. Section E, Structure reports online·2015

See all related articles

Search research articles

Related Experiment Video

Updated: Jun 1, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

4-Chloro-2,6-dinitro-phenol.

¹Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

This study details the molecular structure of a chlorinated nitroaromatic compound. It reveals specific details about the planarity of its aromatic ring and the positioning of its nitro groups, including hydrogen bonding interactions.

More Related Videos

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Analysis of Organochlorine Pesticides in a Soil Sample by a Modified QuEChERS Approach Using Ammonium Formate

Analysis of Organochlorine Pesticides in a Soil Sample by a Modified QuEChERS Approach Using Ammonium Formate

Published on: January 20, 2023

Related Experiment Videos

Last Updated: Jun 1, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Analysis of Organochlorine Pesticides in a Soil Sample by a Modified QuEChERS Approach Using Ammonium Formate

Analysis of Organochlorine Pesticides in a Soil Sample by a Modified QuEChERS Approach Using Ammonium Formate

Published on: January 20, 2023

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical behavior and properties.
Chlorinated nitroaromatic compounds are significant in various chemical applications, necessitating detailed structural characterization.

Purpose of the Study:

To elucidate the detailed molecular geometry and crystal structure of the compound C(6)H(3)ClN(2)O(5).
To investigate the intramolecular interactions, specifically hydrogen bonding, within the molecule.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
Analysis of the crystal structure included assessing the planarity of the aromatic ring and the orientation of substituents.

Main Results:

The aromatic ring of C(6)H(3)ClN(2)O(5) exhibits near planarity, with a root-mean-square deviation of 0.007 Å.
One nitro group is nearly coplanar with the ring (dihedral angle = 3(1)°), while the other is significantly twisted (dihedral angle = 36(1)°).
An intramolecular hydrogen bond was identified between the phenol hydroxyl group and a coplanar nitro group, forming an S(6) graph-set motif.

Conclusions:

The structural analysis provides precise data on the conformation of this chlorinated nitroaromatic compound.
The observed hydrogen bonding and substituent orientations offer insights into the molecule's stability and potential reactivity.