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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
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...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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...

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4-Chloro-N-(2-methoxy-phen-yl)benzamide.

Aamer Saeed, Rasheed Ahmad Khera, Jim Simpson

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the synthesis and crystal structure of a novel chloro-methoxy-phenyl-amide compound. Analysis reveals near planarity in key molecular segments and specific intermolecular interactions driving crystal packing.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Materials Science

    Background:

    • Amide compounds are crucial in pharmaceuticals and materials.
    • Understanding molecular conformation and crystal packing is key to predicting material properties.

    Purpose of the Study:

    • To synthesize and characterize a novel chloro-methoxy-phenyl-amide compound.
    • To elucidate the molecular structure, including planarity and dihedral angles.
    • To investigate intermolecular interactions and their role in crystal formation.

    Main Methods:

    • Synthesis via refluxing 4-chloro-benzoyl chloride with o-anisidine in chloroform.
    • X-ray crystallography for determining the crystal structure.
    • Analysis of bond angles, dihedral angles, and intermolecular interactions (e.g., N-H⋯O, Cl⋯O, C-H⋯O, C-H⋯π).

    Main Results:

    • The synthesized compound C(14)H(12)ClNO(2) was structurally characterized.
    • The methoxy-phenyl-amide segment exhibits near planarity (dihedral angle 5.10(7)°), stabilized by an intramolecular N-H⋯O interaction.
    • Two benzene rings are inclined at 26.74(7)°, and intermolecular Cl⋯O interactions form dimers, further organized into sheets via C-H⋯O and C-H⋯π interactions.

    Conclusions:

    • The study provides a detailed structural analysis of a novel amide compound.
    • Intramolecular and intermolecular interactions significantly influence the molecular conformation and crystal packing.
    • The findings contribute to the understanding of structure-property relationships in organic crystalline materials.