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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.
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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.
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.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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Related Experiment Video

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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
07:30

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

Published on: January 21, 2020

N'-(Propan-2-yl-idene)nicotinohydrazide.

Feng-Yu Bao, Yu-Xia Zhang, Ying-Xia Zhou

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a compound formed from nicotinohydrazide and acetone. Molecular analysis reveals a specific orientation between the pyridine ring and amide plane, with molecules forming chains via hydrogen bonds.

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure Analysis

    Background:

    • Nicotinohydrazide is a derivative of niacin (vitamin B3) with potential biological activities.
    • Acetone is a common organic solvent and reagent used in synthesis.
    • Understanding the crystal structure of organic compounds is crucial for predicting their physical and chemical properties.

    Purpose of the Study:

    • To synthesize and characterize the crystal structure of the compound formed from nicotinohydrazide and acetone.
    • To analyze the molecular geometry, including the dihedral angle between the pyridine ring and the amide plane.
    • To investigate the intermolecular interactions responsible for crystal packing.

    Main Methods:

    • Condensation reaction between nicotinohydrazide and acetone to form the target compound.
    • Single-crystal X-ray diffraction to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonding).

    Main Results:

    • The title compound, C(9)H(11)N(3)O, was successfully synthesized and its crystal structure elucidated.
    • A dihedral angle of 36.28(10)° was observed between the pyridine ring and the amide plane.
    • Intermolecular N-H⋯O hydrogen bonds were identified, leading to the formation of one-dimensional chains in the crystal lattice.

    Conclusions:

    • The crystal structure provides detailed insights into the solid-state arrangement of the nicotinohydrazide-acetone condensation product.
    • The observed dihedral angle and hydrogen bonding patterns are key factors governing the compound's crystal packing.
    • This structural information can be valuable for further studies on the compound's properties and potential applications.