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Related Experiment Video

Updated: Feb 6, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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2,2-Dichloro-N-(3-nitro-phen-yl)acetamide.

B Thimme Gowda, Sabine Foro, Hartmut Fuess

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    The N-H bond conformation in 3NPDCA is anti to the nitro group, mirroring related acetanilides. Molecules form chains via intermolecular hydrogen bonds, revealing structural similarities in this chemical class.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Acetanilides are a significant class of organic compounds with diverse applications.
    • Understanding the molecular conformation and intermolecular interactions is crucial for predicting chemical properties.
    • Previous studies have characterized various substituted acetanilides, providing a basis for comparison.

    Purpose of the Study:

    • To determine the crystal structure of 3NPDCA (C(8)H(6)Cl(2)N(2)O(3)).
    • To analyze the conformation of the N-H bond in relation to substituent groups.
    • To investigate intermolecular interactions, specifically hydrogen bonding, in the solid state.

    Main Methods:

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

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  • Geometric parameters were analyzed and compared with related compounds.
  • Intermolecular interactions were identified through crystallographic analysis.

    • Main Results:

    • The N-H bond in 3NPDCA adopts an anti conformation relative to the meta-nitro group.
    • This conformation is consistent with that observed in related compounds like 3NPCA and 3NPTCA.
    • Geometric parameters of 3NPDCA are comparable to other substituted acetanilides.
    • Molecules are linked into chains along the b axis by intermolecular N-H⋯O hydrogen bonds.

    Conclusions:

    • The structural and conformational features of 3NPDCA align with those of other meta-substituted acetanilides.
    • Intermolecular hydrogen bonding plays a key role in the crystal packing of 3NPDCA.
    • The study contributes to the understanding of structure-property relationships in acetanilide derivatives.