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Reactions at the Benzylic Position: Halogenation

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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...

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3-Chloro-benzohydrazide.

Uzma Ashiq, Rifat Ara Jamal, Muhammad Nadeem Arshad

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a novel chloro-substituted aromatic hydrazide compound. It reveals specific dihedral angles and intermolecular hydrogen bonding patterns, including R(2)(2)(10) motifs and zigzag chains, influencing molecular assembly.

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Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
Aromatic hydrazides are versatile functional groups with applications in pharmaceuticals and materials science.
Detailed structural analysis provides insights into intermolecular interactions and crystal packing.

Purpose of the Study:

To elucidate the three-dimensional crystal structure of the title compound, C(7)H(7)ClN(2)O.
To characterize the hydrogen bonding network and conformational preferences within the crystal lattice.
To provide a foundation for further studies on structure-property relationships.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and dihedral angles provided conformational information.
Hydrogen bonding interactions were identified and characterized using geometric criteria and graph-set notation.

Main Results:

The hydrazide group exhibits a dihedral angle of 32.30(11)° relative to the benzene ring.
Intermolecular N-H⋯O hydrogen bonds form 10-membered rings (R(2)(2)(10) motif) between adjacent molecules.
Further intermolecular hydrogen bonding creates zigzag chains along the b-axis, and an intramolecular interaction forms a five-membered ring.

Conclusions:

The crystal structure is stabilized by a combination of intermolecular and intramolecular hydrogen bonds.
The identified hydrogen bonding motifs dictate the specific packing arrangement in the solid state.
This structural data serves as a reference for understanding the behavior of related aromatic hydrazide derivatives.