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Related Concept Videos

Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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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.
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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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(E)-2-{(2-Hydroxy-naphthalen-1-yl)methyl-ene}hydrazinecarboxamide.

Yousef M Hijji, Oyebola Oladeinde, Ray J Butcher

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

    This study details the molecular structure and crystal packing of a naphthalene derivative, revealing specific dihedral angles and hydrogen bonding patterns. These interactions form a unique zigzag hydrogen-bonded network, confirmed by computational analysis.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Computational Chemistry

    Background:

    • Understanding molecular interactions is crucial for materials science.
    • Naphthalene derivatives exhibit diverse structural and chemical properties.

    Purpose of the Study:

    • To elucidate the crystal structure and hydrogen bonding of a specific naphthalene derivative (C(12)H(11)N(3)O(2)).
    • To investigate the influence of hydrogen bonding on the molecular arrangement in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction analysis.
    • MOPAC PM3 computational calculations.

    Main Results:

    • The molecule exhibits a dihedral angle of 28.9° between naphthalene and carboxamide groups.
    • Complex bifurcated hydrogen bonding involving amide and hydroxyl groups was observed.
    • A 1D zigzag hydrogen-bonded network along the (101) plane was formed by linked molecules.
    • Adjacent naphthalene groups in the chain showed a dihedral angle of 86.9°.

    Conclusions:

    • The crystal packing is dominated by extensive N-H⋯O hydrogen bonding.
    • The observed hydrogen-bonded network is a key feature of this molecule's solid-state structure.
    • Computational results support the experimentally determined structural features.