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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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.
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...

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Related Experiment Video

Updated: May 24, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

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Published on: March 6, 2019

4-(Pyridin-2-yl)-1,3-dithiol-2-one.

Guoquan Zhou, Xinzhi Chen

    Acta Crystallographica. Section E, Structure Reports Online
    |February 21, 2012
    PubMed
    Summary

    The crystal structure of C(8)H(5)NOS(2) reveals near-planar rings with a slight dihedral angle. Intermolecular interactions, including hydrogen bonds and sulfur-sulfur contacts, stabilize the crystal packing.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
    • Crystal packing forces significantly influence a compound's physical and chemical behavior.
    • Sulfur-containing heterocyclic compounds often exhibit unique electronic and structural characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the novel compound C(8)H(5)NOS(2).
    • To analyze the planarity of the molecule and the dihedral angle between its ring systems.
    • To identify and describe the intermolecular interactions responsible for crystal stabilization.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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    Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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    Published on: April 9, 2018

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    Published on: April 9, 2018

  • Analysis of atomic deviations from least-squares planes provided insights into molecular planarity.
  • Intermolecular geometric parameters, including hydrogen bonds and S⋯S contacts, were calculated.

    • Main Results:

    • The non-hydrogen atoms of C(8)H(5)NOS(2) were found to be approximately coplanar, with a maximum deviation of 0.060(3) Å.
    • A small dihedral angle of 5.96(17)° was observed between the pyridine and 1,3-dithiol-2-one ring planes.
    • Crystal packing is characterized by weak intermolecular C-H⋯O hydrogen bonds and a short S⋯S contact of 3.510(5) Å.

    Conclusions:

    • The crystal structure of C(8)H(5)NOS(2) is well-defined, showcasing a near-planar conformation.
    • The observed intermolecular interactions, particularly the S⋯S contact, play a significant role in the compound's solid-state architecture.
    • These findings contribute to the understanding of structure-property relationships in sulfur-containing heterocycles.