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Related Concept Videos

Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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

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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...
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

N-(3-Methyl-phen-yl)benzamide.

B Thimme Gowda, Sabine Foro, B P Sowmya

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

    This study details the crystal structure of a C(14)H(13)NO compound, revealing hydrogen-bonded chains and significant twisting between aromatic rings in its molecular conformation.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding molecular conformation and intermolecular interactions is crucial in solid-state chemistry.
    • Crystal structure analysis provides detailed insights into the spatial arrangement of atoms and molecules.
    • Hydrogen bonding plays a significant role in determining crystal packing and material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(14)H(13)NO.
    • To characterize the hydrogen bonding network and molecular conformation.
    • To investigate the orientation of functional groups and aromatic rings within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided conformational details.
    • Hydrogen bond analysis (N-H⋯O) was performed to identify intermolecular interactions.

    Main Results:

    • The asymmetric unit contains four molecules forming two symmetry-independent chains linked by N-H⋯O hydrogen bonds.
    • Amide groups exhibit trans orientation of N-H and C=O bonds.
    • Significant twisting between the two aromatic rings (dihedral angles 70.6–74.2°) and non-planar molecular geometry were observed.
    • One molecule displays disorder in the aniline fragment, with anti and syn conformers occupying the same site.

    Conclusions:

    • The crystal structure of C(14)H(13)NO is characterized by specific hydrogen bonding and significant conformational flexibility.
    • The observed molecular twisting and disorder provide insights into packing forces and potential polymorphic behavior.
    • This structural data contributes to the understanding of structure-property relationships in organic crystalline materials.