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Related Concept Videos

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.
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...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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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.
Nomenclature of Aromatic Compounds with a Single Substituent01:23

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: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
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...

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N-(1-Naphth-yl)benzene-sulfonamide.

Sifang Zhang1, Yuewen Zhang, Chuntao Wang

  • 1Department of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary

This study details the crystal structure of a novel organic compound, C(16)H(13)NO(2)S. Molecular analysis reveals specific torsion and dihedral angles, along with intermolecular hydrogen bonding and pi-pi interactions influencing crystal packing.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Area of Science:

  • Crystallography and Molecular Structure
  • 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 bonding and pi-pi interactions, play a significant role in the self-assembly and stability of crystal structures.
  • Detailed structural analysis provides fundamental insights into the solid-state behavior of novel chemical entities.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(16)H(13)NO(2)S.
  • To quantify key conformational parameters, including torsion and dihedral angles.
  • To identify and characterize intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of crystallographic data to calculate torsion angles (C-SO(2)-NH-C) and dihedral angles between aromatic ring systems.
  • Identification of hydrogen bonding and pi-pi stacking interactions within the crystal lattice.

Main Results:

  • The C-SO(2)-NH-C torsion angle was determined to be -70.1(2)°.
  • The dihedral angle between the naphthyl and phenyl ring systems was measured at 34.67(4)°.
  • Intermolecular N-H⋯O hydrogen bonds form chains along the [100] direction, and pi-pi interactions between naphthyl groups exhibit an inter-planar spacing of 3.541(3) Å.

Conclusions:

  • The crystal structure of C(16)H(13)NO(2)S is characterized by specific torsional and dihedral angles, indicating a defined molecular conformation.
  • The crystal packing is significantly influenced by intermolecular N-H⋯O hydrogen bonds and pi-pi stacking interactions, leading to chain formation.
  • These findings provide a structural basis for understanding the solid-state properties and potential applications of this organic compound.