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Related Concept Videos

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.
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.
Sulfur Assimilation01:20

Sulfur Assimilation

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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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).

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Related Experiment Video

Updated: Jun 1, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Bis(phenyl-sulfin-yl)methane.

Solange M S V Wardell, Geraldo M de Lima, James L Wardell

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

    The crystal structure of C(13)H(12)O(2)S(2) reveals two independent molecules with slight differences in benzene ring orientation. These molecules form supramolecular chains via hydrogen bonding and pi-stacking interactions.

    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Understanding molecular arrangements in crystals is crucial for predicting material properties.
    • The title compound, C(13)H(12)O(2)S(2), presents an interesting case for structural analysis due to its potential for varied molecular conformations.
    • Previous studies on similar organosulfur compounds have highlighted the importance of intermolecular interactions in dictating crystal packing.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(13)H(12)O(2)S(2).
    • To analyze the differences in molecular conformation between independent molecules within the asymmetric unit.
    • To identify and characterize the intermolecular interactions responsible for the observed crystal packing.

    Main Methods:

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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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    Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
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    Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)
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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.
    • Intermolecular interactions, including hydrogen bonds (C-H⋯O) and pi-stacking (C-H⋯π), were identified using crystallographic software.

    Main Results:

    • The asymmetric unit contains two independent molecules of C(13)H(12)O(2)S(2) with minor variations in benzene ring orientations, indicated by distinct O-S-C-C torsion angles.
    • Supramolecular chains aligned along the a axis were observed, stabilized by C-H⋯O hydrogen bonds.
    • These chains are further interconnected in the three-dimensional crystal lattice through C-H⋯π interactions.

    Conclusions:

    • The crystal structure of C(13)H(12)O(2)S(2) is characterized by the presence of two conformationally distinct molecules in the asymmetric unit.
    • The crystal packing is governed by a combination of C-H⋯O and C-H⋯π interactions, leading to the formation of extended supramolecular structures.
    • These findings contribute to the understanding of structure-property relationships in organosulfur compounds.