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Related Concept Videos

Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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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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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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Sulfonated 1,3-bis-(4-pyrid-yl)propane.

Ore Kuyinu, Andrew P Purdy, Ray J Butcher

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the zwitterionic structure of a novel pyridinium sulfonate compound. Its butterfly-like conformation and chiral packing are influenced by strong intermolecular hydrogen bonding, impacting crystal structure.

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    Area of Science:

    • Crystallography and Molecular Structure
    • Supramolecular Chemistry
    • Organic Chemistry

    Background:

    • Understanding the solid-state behavior of organic molecules is crucial for materials science.
    • Zwitterionic compounds, possessing both positive and negative charges, exhibit unique structural and electronic properties.
    • Pyridinium derivatives are widely studied for their diverse applications.

    Purpose of the Study:

    • To elucidate the crystal structure and molecular conformation of 4-[3-(3-sulfonato-pyridin-1-ium-4-yl)prop-yl]pyridin-1-ium-3-sulfonate.
    • To investigate the intermolecular interactions governing the packing of this zwitterionic compound.
    • To characterize the chirality arising from the molecular conformation.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
    • Analysis of bond lengths, angles, and dihedral angles characterized the molecular conformation.
    • Intermolecular interactions, including hydrogen bonding and C-H···O contacts, were identified and analyzed.

    Main Results:

    • The compound crystallizes as a zwitterion, with proton transfer from sulfonic acid to the pyridine nitrogen.
    • A distinct butterfly-like conformation was observed, with a dihedral angle of 83.56° between the pyridinium rings.
    • Strong intermolecular hydrogen bonding and weaker C-H···O interactions dictate the crystal packing, leading to chiral arrangements.

    Conclusions:

    • The zwitterionic nature and butterfly conformation significantly influence the crystal packing of this pyridinium sulfonate.
    • The observed chirality in conformation and packing highlights the importance of intermolecular forces in supramolecular assembly.
    • This structural characterization provides fundamental insights into the solid-state behavior of related zwitterionic organic compounds.