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Related Concept Videos

Electrophilic Addition to Alkynes: Halogenation02:38

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.
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Alkyl Halides02:45

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...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Diazonium Group Substitution: –OH and –H01:19

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.

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Related Experiment Video

Updated: Jun 1, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

3-Cyano-anilinium iodide monohydrate.

Jing Dai1, Xin-Yuan Chen

  • 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
|May 19, 2011
PubMed
Summary

The crystal structure reveals chains of organic cations linked by hydrogen bonds. These chains form sheets connected into a 3D network through various hydrogen bonds and pi-pi interactions.

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Understanding the self-assembly of organic molecules is crucial for designing new materials.
  • Hydrogen bonding and pi-pi interactions are key non-covalent forces governing crystal packing.
  • The title compound, C(7)H(7)N(2) (+)·I(-)·H(2)O, presents an interesting case for studying these interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound.
  • To investigate the role of hydrogen bonding and pi-pi interactions in the formation of the 3D network.
  • To characterize the supramolecular assembly of the organic cation, iodide anion, and water molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of hydrogen bond distances and angles was performed.
  • Identification and analysis of pi-pi stacking interactions were conducted.

Main Results:

  • The crystal structure consists of [C(7)H(7)N(2) (+)](n) chains along the a-axis, linked by N-H⋯N hydrogen bonds.
  • Cations, anions (iodide), and water molecules form sheets parallel to the ac plane via N-H⋯I, N-H⋯O, and O-H⋯I hydrogen bonds.
  • Pi-pi interactions (centroid-centroid distance = 3.8378(7) Å) connect these sheets into a three-dimensional network.

Conclusions:

  • The title compound exhibits a complex 3D supramolecular network driven by a combination of hydrogen bonding and pi-pi interactions.
  • The crystal packing highlights the interplay between organic cations, inorganic anions, and solvent molecules in directing self-assembly.
  • This structural insight contributes to the understanding of crystal engineering principles for related systems.