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Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

Nucleophilic Aromatic Substitution: Elimination–Addition

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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...

Sulfur Assimilation

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Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to become...

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

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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...

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Published on: July 28, 2022

Benzyl-sulfamide.

Thomas Gelbrich¹, Mairi F Haddow, Ulrich J Griesser

¹Institute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria.

Acta Crystallographica. Section E, Structure Reports Online

|July 15, 2011

Summary

This summary is machine-generated.

The crystal structure of 4-(benzyl-amino)-benzene-sulfonamide reveals a unique hydrogen-bonded ladder framework. This arrangement is formed by specific interactions between its amino and sulfonyl groups.

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Area of Science:

Crystallography
Supramolecular Chemistry
Materials Science

Background:

Understanding molecular interactions is crucial for designing novel materials.
Hydrogen bonding plays a significant role in the self-assembly of crystalline structures.
Benzene sulfonamide derivatives are known for diverse biological and material properties.

Purpose of the Study:

To elucidate the crystal structure of 4-(benzyl-amino)-benzene-sulfonamide.
To investigate the intermolecular interactions, particularly hydrogen bonding, within the crystal lattice.
To characterize the resulting supramolecular architecture.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
Analysis of hydrogen bonding networks and their contribution to the crystal packing.
Identification of specific hydrogen bond donors and acceptors.

Main Results:

The crystal structure of 4-(benzyl-amino)-benzene-sulfonamide (C(13)H(14)N(2)O(2)S) was successfully determined.
Molecules form a hydrogen-bonded framework structure through N-H⋯O interactions.
A characteristic hydrogen-bonded ladder structure, featuring fused R(2)(2)(8) rings, was observed along the a axis.

Conclusions:

The study reveals a well-defined hydrogen-bonded ladder architecture in 4-(benzyl-amino)-benzene-sulfonamide crystals.
The NH(2) groups and sulfonyl oxygen atoms are key participants in forming the observed supramolecular framework.
The findings contribute to the understanding of crystal engineering principles for sulfonamide-based compounds.