Related Experiment Video
Updated: May 21, 2026
11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
2-Amino-N'-phenyl-benzohydrazide.
Summary
This study details the molecular structure and crystal packing of a novel organic compound. Analysis reveals specific dihedral angles, intramolecular hydrogen bonding, and a 2D network formed by intermolecular interactions including pi-pi stacking.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
- Intermolecular forces, such as hydrogen bonding and pi-pi stacking, dictate crystal packing and influence bulk material characteristics.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(13)H(13)N(3)O.
- To analyze the molecular conformation, including dihedral angles between aromatic rings and the NNCO unit.
- To investigate the intermolecular interactions and network formation within the crystal lattice.
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 insights into molecular geometry.
- Identification and characterization of hydrogen bonds and other non-covalent interactions were performed.
Main Results:
- The NNCO unit exhibits dihedral angles of 35.8° and 84.0° with the benzene and phenyl rings, respectively.
- A significant dihedral angle of 61.2° was observed between the two aromatic rings.
- An intramolecular N-H⋯O hydrogen bond was identified, along with intermolecular N-H⋯O and N-H⋯N hydrogen bonds forming a 2D network.
- Pi-pi stacking interactions between phenyl rings with a centroid-centroid distance of 3.803 Å were observed.
Conclusions:
- The crystal structure of C(13)H(13)N(3)O is characterized by specific conformational preferences and extensive intermolecular interactions.
- The formation of a 2D network through hydrogen bonding and pi-pi stacking highlights the importance of supramolecular assembly in the solid state.
- These findings provide a foundation for understanding the structure-property relationships of this class of organic compounds.
More Related Videos
Related Concept Videos
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:20Electrophilic 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.
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
01:11Nucleophilic 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...
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
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...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...