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Related Concept Videos

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).
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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.
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...
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...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

N-Phenyl-tert-butane-sulfinamide.

Mritunjoy Datta, Alan J Buglass, Mark R J Elsegood

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study analyzes the crystal structure of a racemic compound, C(10)H(15)NOS. It reveals unique molecular packing driven by hydrogen bonds and a notably short N-C(aryl) bond, differing from typical N-alkyl-alkanesulfinamides.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Sulfinamides are versatile organic compounds with applications in synthesis and medicinal chemistry.
    • Understanding the solid-state structure of sulfinamides provides insights into their chemical properties and intermolecular interactions.
    • The title compound, C(10)H(15)NOS, is a racemic mixture whose crystal packing has not been previously detailed.

    Purpose of the Study:

    • To elucidate the crystal structure of the racemic title compound, C(10)H(15)NOS.
    • To analyze the intermolecular interactions, specifically hydrogen bonding, governing the crystal packing.
    • To compare the observed N-C(aryl) bond length with those typically found in related N-alkyl-alkanesulfinamides.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.

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  • Crystal structure analysis involved identifying molecular symmetry, hydrogen bonding networks, and bond lengths.
  • Geometric parameters, including bond lengths and angles, were precisely measured and compared.
  • Main Results:

    • The crystal packing of the racemic title compound features centrosymmetric molecular pairs.
    • These pairs are linked by N-H⋯O=S hydrogen bonds, arranged in a head-to-tail fashion.
    • A significant finding is the N-C(aryl) bond length of 1.4083(12) Å, which is considerably shorter than those (1.470–1.530 Å) typically observed in N-alkyl-alkanesulfinamides.

    Conclusions:

    • The crystal structure of C(10)H(15)NOS is characterized by specific hydrogen bonding and a short N-C(aryl) bond.
    • This structural feature suggests unique electronic or steric influences within the N-aryl-alkanesulfinamide system.
    • Further studies may explore the implications of this short N-C(aryl) bond on the compound's reactivity and properties.