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Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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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...
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Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
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Thio-phene-2-carbaldehyde 2,4-dinitro-phenyl-hydrazone.

Zhi-Gang Yin, Heng-Yu Qian, He-Ping Li

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

    The crystal structure of C(11)H(8)N(4)O(4)S reveals a nearly planar molecule with a small dihedral angle between its thiophene and benzene rings. Bifurcated hydrogen bonds contribute to the formation of inversion dimers in its crystal lattice.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • The title compound, C(11)H(8)N(4)O(4)S, is a molecule of interest for its structural and bonding characteristics.
    • Understanding the spatial arrangement and intermolecular interactions is crucial for predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(11)H(8)N(4)O(4)S.
    • To analyze the molecular geometry, specifically the dihedral angle between the thiophene and benzene rings.
    • To investigate the hydrogen bonding network and identify any resulting supramolecular motifs.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
    • Hydrogen bond analysis and graph-set methodology were used to characterize intermolecular interactions.

    Main Results:

    • The molecule C(11)H(8)N(4)O(4)S adopts an approximately planar conformation.
    • A small dihedral angle of 5.73(10)° was measured between the thiophene and benzene rings.
    • Bifurcated inter- and intra-molecular N-H⋯(O,O) hydrogen bonds were observed.
    • These intermolecular interactions lead to the formation of inversion dimers with an R(2)(2)(12) graph-set motif.

    Conclusions:

    • The crystal structure of C(11)H(8)N(4)O(4)S is characterized by a near-planar geometry and specific hydrogen bonding patterns.
    • The observed hydrogen bonding network dictates the formation of supramolecular assemblies, specifically inversion dimers.
    • These findings contribute to the understanding of structure-property relationships in organic crystalline materials.