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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.

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.

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 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...

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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(E)-4-Methyl-N'-(3-nitro-benzyl-idene)benzohydrazide.

Hua-Nan Hu¹, Shi-Yong Liu

¹College of Chemistry & Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|June 22, 2012

Summary

This study details the crystal structure of a nitrogen-containing organic compound. Molecular analysis reveals specific dihedral angles and N-H⋯O hydrogen bonding, forming C(4) chains in the crystal lattice.

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

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Published on: November 23, 2016

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Crystal structure analysis provides precise details on molecular conformation and intermolecular interactions.
The compound C(15)H(13)N(3)O(3) is a novel organic molecule with potential applications in materials science.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(15)H(13)N(3)O(3).
To quantify the dihedral angles between the aromatic rings and the nitro group.
To identify and characterize the intermolecular interactions present in the crystalline state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
The crystal structure was solved and refined using standard crystallographic software.
Analysis of hydrogen bonding and conformational parameters was performed.

Main Results:

The crystal structure of C(15)H(13)N(3)O(3) was successfully determined.
A small dihedral angle of 1.01(3)° was observed between the two benzene rings.
The nitro group exhibited a dihedral angle of 5.99(15)° with its attached benzene ring.
Molecules were found to form C(4) chains via N-H⋯O hydrogen bonds along the [010] direction.

Conclusions:

The title compound C(15)H(13)N(3)O(3) exhibits a nearly planar conformation between its benzene rings.
Intermolecular N-H⋯O hydrogen bonding plays a significant role in organizing the crystal structure.
The determined crystal structure provides a foundation for further studies on the compound's physical and chemical properties.