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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

3.8K
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...
3.8K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.0K
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...
4.0K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.8K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.8K
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

3.8K
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...
3.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.9K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.5K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.5K

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Related Experiment Video

Updated: Dec 20, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

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Pyridine-2-carboximidamidate chloride monohydrate.

Qifan Chen, Huidong Zhang, Fang Zhang

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of a pyridine carboximidamidate compound. The analysis reveals a complex three-dimensional network formed by hydrogen bonds between cations, chloride ions, and water molecules.

    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Organic Chemistry

    Background:

    • Understanding the crystal packing and intermolecular interactions of organic compounds is crucial for predicting their physical and chemical properties.
    • Pyridine derivatives are important in various fields, including pharmaceuticals and materials science.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(6)H(8)N(3) (+)·Cl(-)·H(2)O.
    • To investigate the intermolecular interactions, including hydrogen bonding, that govern the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of hydrogen bonding networks (N-H⋯N, N-H⋯Cl, N-H⋯O, O-H⋯Cl) was performed.

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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

    Published on: April 27, 2017

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    Related Experiment Videos

    Last Updated: Dec 20, 2025

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
    14:11

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

    Published on: June 10, 2021

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    One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
    09:45

    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

    Published on: April 27, 2017

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    Main Results:

    • The asymmetric unit contains three formula units of the title compound.
    • Pyridine carboximidamidate cations exhibit non-planar conformations.
    • A three-dimensional network is formed through extensive intermolecular hydrogen bonding involving cations, chloride ions, and water molecules.

    Conclusions:

    • The crystal structure is stabilized by a combination of cation-cation, cation-anion, and cation-water hydrogen bonds.
    • Water molecules and chloride ions also participate in hydrogen bonding, further contributing to the network.
    • The detailed understanding of this crystal structure provides insights into the solid-state behavior of pyridine carboximidamidate derivatives.