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

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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...

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...

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

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...

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).

You might also read

Related Articles

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

Sort by

Same author

(E)-1-(5-Bromo-2-hy-droxy-phen-yl)-3-[4-(dimethyl-amino)-phen-yl]prop-2-en-1-one.

Acta crystallographica. Section E, Structure reports online·2012

Same author

2,4-Dimethyl-anilinium perchlorate.

Acta crystallographica. Section E, Structure reports online·2011

Same author

(R)-2-Methyl-piperazine-1,4-diium tetra-chloridoanti-monate(III) chloride.

Acta crystallographica. Section E, Structure reports online·2011

Same author

2-Carb-oxy-1-phenyl-ethanaminium nitrate.

Acta crystallographica. Section E, Structure reports online·2011

Same author

Bis(2-amino-benzonitrile)tetra-aqua-cobalt(II) dichloride.

Acta crystallographica. Section E, Structure reports online·2011

Same author

Methyl 1-bromo-2-naphthoate.

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 5, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

2-Methyl-5-nitro-benzonitrile.

Wen-Xian Liang¹, Guo-Xi Wang

¹Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a nitrobenzene derivative, C(8)H(6)N(2)O(2). The nitro group shows a slight rotation, and the crystal lattice is stabilized by van der Waals forces.

More Related Videos

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Related Experiment Videos

Last Updated: Jun 5, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding molecular conformations is crucial in organic chemistry.
Nitroaromatic compounds exhibit diverse structural properties.
Crystal packing influences material properties.

Purpose of the Study:

To elucidate the crystal structure of the compound C(8)H(6)N(2)O(2).
To quantify the rotational angle of the nitro group relative to the benzene ring.
To identify the intermolecular forces stabilizing the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed.
The crystal structure was analyzed and refined.
Intermolecular interactions were assessed.

Main Results:

The crystal structure of C(8)H(6)N(2)O(2) was determined.
A significant rotation of 10.2(2)° was observed for the nitro group out of the benzene ring plane.
Van der Waals interactions were identified as the primary stabilizing forces in the crystal.

Conclusions:

The molecular geometry of C(8)H(6)N(2)O(2) is characterized by a notable nitro group torsion.
The crystal packing is dominated by weak van der Waals forces.
This structural information provides a basis for understanding the physical properties of related nitroaromatic compounds.