Related Experiment Video
Updated: Jun 5, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
4-Chloro-N-(2,6-dimethyl-phen-yl)benzamide
The crystal structure of N26DMP4CBA reveals anti conformations of N-H and C=O bonds, with significant tilting of the central amide group across three molecules. Intermolecular hydrogen bonds form infinite chains, and one xylyl group exhibits disorder.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Benzanilides are a significant class of organic compounds with diverse applications.
- Understanding the conformational preferences of amide bonds is crucial for predicting molecular properties and reactivity.
- Previous studies have established general conformational trends in benzanilide derivatives.
Purpose of the Study:
- To elucidate the detailed crystal structure of N26DMP4CBA (C(15)H(14)ClNO).
- To analyze the conformational characteristics of the amide group and aromatic rings within the unit cell.
- To investigate intermolecular interactions and their role in crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of N26DMP4CBA.
- Crystallographic data were analyzed to determine bond lengths, bond angles, dihedral angles, and intermolecular interactions.
- Disorder in specific molecular groups was modeled and refined.
Main Results:
- The N-H and C=O bonds in N26DMP4CBA adopt an anti conformation, consistent with other benzanilides.
- Three molecules exist in the asymmetric unit, each displaying distinct tilting angles of the central amide group relative to the benzoyl ring (45.2°, 21.2°, 14.9°).
- Dihedral angles between the benzoyl and aniline rings vary significantly (39.9°, 51.0°, 86.3°), and intermolecular N-H⋯O hydrogen bonds create infinite chains along the [101] direction. One xylyl group shows positional disorder.
Conclusions:
- The crystal structure of N26DMP4CBA provides detailed insights into its molecular conformation and packing.
- The observed conformational variations and hydrogen bonding patterns highlight the flexibility and intermolecular interactions in benzanilide derivatives.
- The study contributes to the understanding of structure-property relationships in this class of compounds.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
11:01Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
Related Concept Videos
NMR Spectroscopy of Benzene Derivatives
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Reactions at the Benzylic Position: Halogenation