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

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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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...

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.

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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...

You might also read

Related Articles

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

Sort by

Same author

Crystal structures of 2,4,6-tri-iodo-benzo-nitrile and 2,4,6-tri-iodo-phenyl isocyanide.

Acta crystallographica. Section E, Crystallographic communications·2018

Same author

Two new polytypes of 2,4,6-tri-bromo-benzo-nitrile.

Acta crystallographica. Section E, Crystallographic communications·2016

Same author

Unexpectedly Stable (Chlorocarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane, and Related Compounds That Model the Zumach-Weiss-Kühle (ZWK) Reaction for Synthesis of 1,2,4-Dithiazolidine-3,5-diones.

The Journal of organic chemistry·2015

Same author

Four polymorphs (polytypes) of 5,6-dimethylbenzofurazan 1-oxide.

Acta crystallographica. Section B, Structural science·2012

Same author

Planar packing of tetrachlorodicyanobenzenes. II.

Acta crystallographica. Section B, Structural science·2009

Same author

2,4,6-trifluorobenzonitrile.

Acta crystallographica. Section C, Crystal structure communications·2008

Search research articles

Related Experiment Video

Updated: Jul 6, 2026

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

3,4,6-Trichloro-5-cyano-2-hydroxybenzamide.

Doyle Britton¹

¹Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA. britton@chem.umn.edu

Acta Crystallographica. Section C, Crystal Structure Communications

|March 7, 2008

Summary

This study reveals the crystal structure of a novel compound, highlighting the crucial roles of hydrogen bonding and chlorine-nitrogen interactions in its molecular assembly. These interactions facilitate the formation of ribbons, layers, and ultimately, the stable crystal lattice.

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

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

Related Experiment Videos

Last Updated: Jul 6, 2026

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

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

Area of Science:

Crystallography
Supramolecular Chemistry
Organic Chemistry

Background:

Understanding the intermolecular forces that govern crystal packing is fundamental in materials science.
The title compound, C(8)H(3)Cl(3)N(2)O(2), presents an interesting case for studying complex interactions due to its functional groups.

Purpose of the Study:

To elucidate the crystal structure of the title compound.
To identify and analyze the key intermolecular interactions responsible for the observed crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
Analysis of the crystal structure focused on identifying hydrogen bonds, halogen bonds (Cl...N), and pi-pi stacking interactions.

Main Results:

The crystal structure reveals that hydrogen bonding and Cl...N interactions are equally significant in stabilizing the crystal lattice.
Molecules self-assemble into ribbons through cyclic (CONH)(2) and cyclic (ClCCC[triple-bond]N)(2) interactions.
Ribbons further organize into layers via Cl...Cl interactions, with layers connected by NH...N[triple-bond]C hydrogen bonds and pi-pi stacking.

Conclusions:

The crystal structure of C(8)H(3)Cl(3)N(2)O(2) is dictated by a combination of hydrogen bonding, Cl...N, Cl...Cl, and pi-pi interactions.
This intricate network of interactions leads to a stable, layered supramolecular architecture.