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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Preparation of Amides01:29

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...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

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Related Experiment Video

Updated: May 21, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

2-Amino-ethanaminium iodide.

Alan R Kennedy, Maurice O Okoth

    Acta Crystallographica. Section E, Structure Reports Online
    |June 22, 2012
    PubMed
    Summary

    The title salt exhibits a unique helical chain structure formed by strong intermolecular hydrogen bonding between ammonium and amine groups. Iodide anions are situated in channels alongside these cation chains.

    Area of Science:

    • Crystal engineering
    • Supramolecular chemistry
    • Materials science

    Background:

    • Understanding the self-assembly of organic salts is crucial for designing novel materials.
    • Hydrogen bonding plays a pivotal role in dictating crystal structures and properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title salt, [NH(3)CH(2)CH(2)NH(2)](+)·I(-).
    • To investigate the role of intermolecular interactions in the formation of the observed array structure.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
    • Analysis of hydrogen bonding networks and their contribution to the overall architecture.

    Main Results:

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

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

    Published on: March 24, 2018

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    Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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    Published on: May 16, 2014

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

    • The title salt self-assembles into a helical chain structure of cations, stabilized by strong intermolecular N-H⋯N hydrogen bonds.
    • Iodide anions are located in channels that run parallel to the helical cation chains.
    • Each ammonium group and amine group participates in hydrogen bonding, either with adjacent cations or with iodide anions.

    Conclusions:

    • The crystal structure is dominated by a robust hydrogen bonding network involving both cation-cation and cation-anion interactions.
    • The observed helical arrangement highlights the directional nature of hydrogen bonding in directing crystal packing.
    • This study provides insights into the structure-property relationships of organic salts with potential applications in materials science.