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Nucleophilic Aromatic Substitution: Elimination–Addition

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...

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

Electrophilic Aromatic Substitution: Nitration of Benzene

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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.

Formation of Halohydrin from Alkenes

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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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Updated: Jun 1, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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N'-[(E)-1-(5-Bromo-2-hydroxy-phen-yl)ethyl-idene]benzohydrazide.

Chang-Zheng Zheng, Chang-You Ji, Xiu-Li Chang

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a bromo-organic compound, revealing a transE configured C=N double bond and specific aromatic ring orientation. Hydrogen bonds play a key role in stabilizing its crystal lattice.

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Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Understanding molecular geometry and intermolecular forces is crucial in organic chemistry.
Crystal structure analysis provides detailed insights into the spatial arrangement of atoms and molecules.

Purpose of the Study:

To elucidate the precise three-dimensional structure of the title compound, C(15)H(13)BrN(2)O(2).
To investigate the stereochemistry of the C=N double bond and the spatial relationship between aromatic rings.
To identify and characterize the hydrogen bonding network within the crystal structure.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of bond lengths, bond angles, and dihedral angles provided geometric information.
Identification of hydrogen bond donors and acceptors was performed.

Main Results:

The C=N double bond was confirmed to have a trans (E) configuration.
The dihedral angle between the two aromatic ring planes was measured at 22.3(1)°.
Intra-molecular O-H⋯O and inter-molecular N-H⋯O hydrogen bonds were identified as key stabilizing interactions.

Conclusions:

The crystal structure of C(15)H(13)BrN(2)O(2) is well-defined with a specific stereochemistry at the C=N bond.
The observed dihedral angle indicates a non-planar arrangement of the aromatic systems.
Hydrogen bonding significantly contributes to the overall stability of the crystal lattice.