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Related Concept Videos

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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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.
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.

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Updated: Jun 1, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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N,N'-Diphenyl-suberamide.

B Thimme Gowda, Miroslav Tokarčík, Vinola Z Rodrigues

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

    This study details the crystal structure of N,N'-diphenyl-octanediamide, revealing phenyl rings at a 76.5° angle. Intermolecular hydrogen bonds form molecular chains, crucial for understanding its solid-state properties.

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    Area of Science:

    • Solid-state chemistry
    • Crystallography
    • Organic chemistry

    Background:

    • Understanding the solid-state structure of organic molecules is essential for predicting their physical and chemical properties.
    • Amide compounds, like N,N -diphenyl-octanediamide, exhibit diverse structural motifs influenced by intermolecular interactions.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of N,N -diphenyl-octanediamide.
    • To investigate the role of intermolecular interactions, specifically hydrogen bonding, in stabilizing the crystal lattice.
    • To characterize the spatial arrangement of phenyl rings within the crystal structure.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and intermolecular distances was performed.
    • Identification and analysis of hydrogen bonding networks and their contribution to crystal packing.

    Main Results:

    • The crystal structure of N,N -diphenyl-octanediamide (C(20)H(24)N(2)O(2)) was successfully determined.
    • The two phenyl rings exhibit a significant inter-planar angle of 76.5(2)°.
    • Intermolecular N-H⋯O hydrogen bonds were identified, linking molecules into chains along the b-axis, and the crystal was found to be non-merohedrally twinned.

    Conclusions:

    • The crystal structure is primarily stabilized by a network of intermolecular N-H⋯O hydrogen bonds, dictating the formation of 1D chains.
    • The observed inter-planar angle of the phenyl rings suggests a specific conformation in the solid state.
    • The presence of non-merohedral twinning is an important characteristic of the crystal studied.