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Related Concept Videos

Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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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.
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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.
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Amines to Sulfonamides: The Hinsberg Test01:23

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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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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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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...
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2-Chloro-N-(3-meth-oxy-benzo-yl)benzene-sulfonamide.

P A Suchetan1, B S Palakshamurthy, G R Mamatha

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Acta Crystallographica. Section E, Structure Reports Online
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Summary

This study details the crystal structure of a chloro- and meth-oxy-substituted benzene derivative. Molecular interactions observed include hydrogen bonds, C-H⋯O interactions, and aromatic π-π stacking, revealing key crystal packing features.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the solid-state behavior of organic molecules is crucial for predicting their physical and chemical properties.
  • Substituted benzene rings can exhibit diverse intermolecular interactions influencing crystal packing.
  • Hydrogen bonding and π-π stacking are fundamental non-covalent interactions in crystal engineering.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a specific chloro- and meth-oxy-substituted benzene compound.
  • To characterize the dihedral angle between the substituted benzene rings.
  • To identify and analyze the types of interactions (hydrogen bonds, C-H⋯O, π-π stacking) governing crystal assembly.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
  • Analysis of the crystal structure identified hydrogen bond donors and acceptors.
  • Intermolecular interactions, including C-H⋯O interactions and π-π stacking, were analyzed based on distances and geometry.

Main Results:

  • The dihedral angle between the chloro- and meth-oxy-substituted benzene rings was determined to be 87.40(1)°.
  • Adjacent molecules form inversion-related dimers via strong N-H⋯O hydrogen bonds, creating R2(2)(8) loops.
  • Further connections through C-H⋯O interactions form C(11) chains and R2(2)(14) loops, alongside aromatic π-π stacking with a centroid-centroid separation of 3.8574(1) Å.

Conclusions:

  • The crystal structure is stabilized by a combination of hydrogen bonding, C-H⋯O interactions, and π-π stacking.
  • These interactions dictate the formation of dimers and extended chain structures in the solid state.
  • The findings provide insights into the supramolecular assembly of substituted aromatic compounds.