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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic 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...
Diazonium Group Substitution: –OH and –H01:19

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.
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

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.
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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N-[(2-Chloro-phen-yl)sulfon-yl]-3-nitro-benzamide.

S Sreenivasa1, D Darshan, T N Lohith

  • 1Department of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India.

Acta Crystallographica. Section E, Structure Reports Online
|September 19, 2013
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a novel chlorinated organic compound, C13H9ClN2O5S. Molecular analysis reveals specific dihedral angles and intermolecular hydrogen bonding critical for its crystal lattice formation.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Crystal structure analysis provides detailed insights into molecular conformation and intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C13H9ClN2O5S.
  • To analyze the molecular geometry, including dihedral angles and torsional conformations.
  • To investigate intermolecular interactions, such as hydrogen bonding and C-H···π interactions, 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 geometric information.
  • Intermolecular interactions were identified and characterized using hydrogen bond analysis and non-covalent interaction analysis.

Main Results:

  • The crystal structure of C13H9ClN2O5S was successfully determined.
  • A significant dihedral angle of 74.86° was observed between the two benzene rings.
  • The molecule exhibits a twisted conformation at the sulfur atom, with a dihedral angle of 82.53° between the sulfonyl benzene ring and the S-N-C=O moiety.
  • Inversion dimers linked by N-H⋯O hydrogen bonds (R2(2)(8) loops) and C(7) [010] chains formed by C-H⋯O hydrogen bonds were identified.
  • Weak C-H⋯π interactions were also observed in the crystal packing.

Conclusions:

  • The study provides a detailed structural characterization of C13H9ClN2O5S.
  • The observed molecular conformation and intermolecular interactions dictate the crystal packing and may influence the compound's physical and chemical properties.
  • The findings contribute to the understanding of structure-property relationships in related organic compounds.