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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...

Diazonium Group Substitution: –OH and –H

Diazonium 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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium 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...

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic 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.

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

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...

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(E)-N'-(2-Furylmethyl-ene)benzo-hydrazide.

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¹College of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China.

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|May 18, 2011

Summary

This study details the crystal structure of a novel organic compound, C(12)H(10)N(2)O(2). Molecular analysis reveals a significant dihedral angle between its benzene and furan rings, with intermolecular interactions observed.

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Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Intermolecular forces, such as hydrogen bonds and van der Waals interactions, play a significant role in the assembly and stability of crystal structures.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(12)H(10)N(2)O(2).
To quantify the dihedral angle between the aromatic (benzene) and heteroaromatic (furan) rings.
To identify and describe the intermolecular interactions present in the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Crystallographic data were analyzed to measure bond lengths, bond angles, and dihedral angles.
Intermolecular interactions, including hydrogen bonds and C-H···π interactions, were identified using standard crystallographic analysis.

Main Results:

The crystal structure of C(12)H(10)N(2)O(2) was successfully determined.
A dihedral angle of 52.54(7)° was measured between the benzene and furan rings, indicating a non-planar conformation.
Intermolecular N-H⋯O hydrogen bonds and C-H⋯π interactions were observed, linking the molecules into a three-dimensional network.

Conclusions:

The title compound exhibits a distinct non-planar conformation due to the dihedral angle between its ring systems.
The crystal packing is stabilized by a combination of hydrogen bonding and C-H⋯π interactions.
The structural insights gained are valuable for understanding structure-property relationships in related organic molecules.