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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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...
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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...

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4-Nitro-phenyl 2-methyl-benzoate.

Uzma Bibi, Humaira M Siddiqi, Michael Bolte

    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(11)NO(4) compound, revealing distinct molecular conformations. Key differences were observed in the dihedral angles between aromatic rings and the coplanarity of nitro groups.

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    Area of Science:

    • Crystallography
    • Molecular structure determination
    • Organic chemistry

    Background:

    • Understanding molecular conformation is crucial in chemistry.
    • C(14)H(11)NO(4) is a compound with potential applications in various chemical fields.
    • Crystallization is a primary method for determining precise molecular geometries.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(14)H(11)NO(4).
    • To analyze the conformational differences between molecules within the asymmetric unit.
    • To investigate the spatial arrangement of functional groups, specifically nitro groups and aromatic rings.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of the asymmetric unit revealed the presence of two distinct molecules.
    • Geometric parameters, including dihedral and torsion angles, were precisely measured.

    Main Results:

    • The title compound, C(14)H(11)NO(4), crystallizes with two molecules in the asymmetric unit.
    • A significant conformational difference was observed in the dihedral angle between the aromatic rings (36.99(5)° and 55.04(5)°).
    • Nitro groups were found to be coplanar with their attached phenyl rings, with specific O-N-C-C torsion angles of -1.9(3)° and 1.0(3)°.

    Conclusions:

    • The crystal structure analysis provides precise geometric data for C(14)H(11)NO(4).
    • The observed conformational variations highlight the flexibility of the molecule in the solid state.
    • The coplanarity of nitro groups suggests specific electronic interactions within the molecule.