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Related Concept Videos

Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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...
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.
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...

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N-Phenyl-anthranilic anhydride.

Guan-Feng Liu1, Yong-Wen Luo, Da-Bin Qin

  • 1School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China.

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

This study details the molecular structure of C(26)H(20)N(2)O(3), revealing its symmetry and stabilization through an intramolecular hydrogen bond. The research provides insights into the compound's specific conformational characteristics.

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Area of Science:

  • Crystallography
  • Molecular Chemistry
  • Organic Chemistry

Background:

  • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Crystallographic studies provide definitive structural data for solid-state compounds.

Purpose of the Study:

  • To elucidate the complete molecular structure of the title compound, C(26)H(20)N(2)O(3).
  • To analyze the conformational features and stabilizing interactions within the molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of crystallographic data to identify symmetry elements and bond types.

Main Results:

  • The molecule C(26)H(20)N(2)O(3) exhibits crystallographic twofold symmetry, with the central oxygen atom on the rotation axis.
  • An intramolecular N-H⋯O hydrogen bond was identified as a key stabilizing feature of the molecular conformation.
  • The dihedral angle between the inner and outer aromatic ring planes was measured at 61.12(5)°.

Conclusions:

  • The determined structure provides a precise description of C(26)H(20)N(2)O(3).
  • The intramolecular hydrogen bond significantly influences the molecule's conformation and stability.
  • This structural information is fundamental for further investigations into the compound's chemical behavior.