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Related Concept Videos

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.
Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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 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.

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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

2-(3,4-Dimethyl-anilino)acetohydrazide.

Muhammad Salim, Zaid Mahmood, M Nawaz Tahir

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study reveals the crystal structure of a novel compound, C(10)H(15)N(3)O, which forms a 2D polymer network through hydrogen bonding. The compound exhibits interesting molecular disorder and specific intermolecular interactions.

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

    Published on: April 27, 2017

    Area of Science:

    • Crystal Engineering
    • Supramolecular Chemistry
    • Organic Chemistry

    Background:

    • Understanding the self-assembly of organic molecules is crucial for designing new materials.
    • Hydrogen bonding plays a key role in directing crystal packing and forming extended structures.
    • Molecular disorder can significantly influence the physical properties of crystalline solids.

    Purpose of the Study:

    • To determine the crystal structure of the title compound, C(10)H(15)N(3)O.
    • To investigate the intermolecular interactions responsible for the observed crystal packing.
    • To characterize the nature and extent of molecular disorder in the crystal.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to elucidate the three-dimensional crystal structure.
    • Analysis of hydrogen bonding networks (N-H⋯O, N-H⋯N) and C-H⋯N interactions was performed.
    • The disorder of the 3,4-dimethyl-phenyl unit was modeled and quantified using occupancy factors.

    Main Results:

    • The compound C(10)H(15)N(3)O crystallizes, forming an infinite two-dimensional polymeric network.
    • Intermolecular N-H⋯O hydrogen bonds are the primary driving force for the network formation.
    • Intramolecular N-H⋯N and intermolecular C-H⋯N interactions were also identified.
    • The 3,4-dimethyl-phenyl group exhibits positional disorder, with two distinct sites and an occupancy ratio of approximately 2:1.
    • A small dihedral angle (2.6°) was observed between the benzene rings of the disordered components.

    Conclusions:

    • The crystal structure of C(10)H(15)N(3)O is characterized by a 2D polymeric network stabilized by hydrogen bonding.
    • The identified intermolecular interactions dictate the supramolecular architecture.
    • The observed molecular disorder in the 3,4-dimethyl-phenyl unit is a significant structural feature that may impact material properties.