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Related Concept Videos

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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(E)-N'-(2,4,6-Trimethyl-benzyl-idene)isonicotinohydrazide.

H S Naveenkumar, Amirin Sadikun, Pazilah Ibrahim

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

    This study details the crystal structure of an isoniazid derivative, revealing its E configuration and specific molecular geometry. Intermolecular hydrogen bonds and C-H⋯π interactions stabilize its crystal lattice.

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

    Published on: January 15, 2018

    Area of Science:

    • Crystallography and Molecular Structure
    • Medicinal Chemistry
    • Organic Chemistry

    Background:

    • Isoniazid is a crucial first-line antituberculosis drug.
    • Derivatives of isoniazid are explored to overcome drug resistance and improve efficacy.
    • Understanding the structural properties of isoniazid derivatives is key to designing new therapeutic agents.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of a novel isoniazid derivative (C(16)H(17)N(3)O).
    • To analyze the stereochemistry, including the configuration around the Schiff base C=N bond.
    • To investigate intermolecular interactions governing the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles to describe molecular conformation.
    • Identification and analysis of intermolecular interactions, such as hydrogen bonds and C-H⋯π interactions.

    Main Results:

    • The isoniazid derivative exhibits an E configuration at the Schiff base C=N bond.
    • The pyridine ring is nearly planar, with a maximum deviation of 0.009(3) Å.
    • Dihedral angles of approximately 38.4° and 39.4° were observed between the hydrazide unit and the pyridine and benzene rings, respectively.
    • Intermolecular N-H⋯O hydrogen bonds link molecules into chains along the [100] direction.
    • Weak intermolecular C-H⋯π interactions further stabilize the crystal structure.

    Conclusions:

    • The study provides a precise structural characterization of the isoniazid derivative.
    • The observed molecular geometry and intermolecular interactions offer insights into the solid-state behavior of this compound.
    • This structural information can be valuable for structure-activity relationship studies and the development of new antitubercular agents.