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N-(3-Chloro-phen-yl)benzamide.

B Thimme Gowda, Miroslav Tokarčík, Jozef Kožíšek

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|January 5, 2011

Summary

This summary is machine-generated.

The N-H bond conformation in N3CPBA is anti to the meta chloro group, differing from some related benzanilides. Molecular structure and hydrogen bonding influence crystal packing in this compound.

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Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Benzanilides are a significant class of organic compounds with diverse applications.
Understanding the conformational preferences of substituents is crucial for predicting molecular properties and reactivity.
Previous studies have explored the impact of chloro-substituents on benzanilide structures.

Purpose of the Study:

To determine the molecular structure and conformation of N3CPBA (C(13)H(10)ClNO).
To investigate the influence of the meta chloro substituent on the N-H bond conformation.
To compare the structural features of N3CPBA with related chlorinated benzanilides.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to elucidate the three-dimensional structure of N3CPBA.
Analysis of bond parameters, dihedral angles, and intermolecular interactions (hydrogen bonding) was performed.
Conformational analysis was conducted by comparing the N-H bond orientation with respect to the chloro substituent.

Main Results:

The N-H bond in N3CPBA adopts an anti conformation relative to the meta chloro substituent on the aniline ring.
This conformation contrasts with the syn conformation observed in N-(2,3-dichloro-phen-yl)benzamide (N23DCPBA).
The dihedral angle between the amide group and the benzoyl ring is 18.2(2)°, and between the two benzene rings is 61.0(1)°. Molecules form chains via N-H⋯O hydrogen bonds along the b axis.

Conclusions:

The meta chloro substituent in N3CPBA dictates an anti N-H bond conformation.
The structural and conformational data provide insights into the structure-property relationships of chlorinated benzanilides.
Intermolecular hydrogen bonding plays a key role in the crystal packing of N3CPBA.